Composition of matter for use in organic light-emitting diodes

ABSTRACT

The present disclosure relates to compounds of Formula (I)-(V) as compounds capable of emitting delayed fluorescence and uses of these compounds in organic light-emitting diodes.

RELATED APPLICATIONS

This application claims the benefit of priority to JP2017-168885 filedSep. 1, 2017; U.S. Provisional Patent Application No. 62/594,837, filedDec. 5, 2017; U.S. Provisional Patent Application No. 62/650,420, filedMar. 30, 2018; U.S. Provisional Patent Application No. 62/653,225, filedApr. 5, 2018; U.S. Provisional Patent Application No. 62/662,548, filedApr. 25, 2018; and U.S. Provisional Patent Application No. 62/664,623,filed Apr. 30, 2018.

BACKGROUND

An organic light emitting diode (OLED) is a light-emitting diode (LED)in which a film of organic compounds is placed between two conductors,which film emits light in response to excitation, such as an electriccurrent. OLEDs are useful in lightings and displays, such as televisionscreens, computer monitors, mobile phones, and tablets. A probleminherent in OLED displays is the limited lifetime of the organiccompounds. OLEDs which emit blue light, in particular, degrade at asignificantly increased rate as compared to green or red OLEDs.

OLED materials rely on the radiative decay of molecular excited states(excitons) generated by recombination of electrons and holes in a hosttransport material. The nature of excitation results in interactionsbetween electrons and holes that split the excited states into brightsinglets (with a total spin of 0) and dark triplets (with a total spinof 1). Since the recombination of electrons and holes affords astatistical mixture of four spin states (one singlet and three tripletsublevels), conventional OLEDs have a maximum theoretical efficiency of25%.

To date, OLED material design has focused on harvesting the remainingenergy from the normally dark triplets. Recent work to create efficientphosphors, which emit light from the normally dark triplet state, haveresulted in green and red OLEDs. Other colors, such as blue, however,require higher energy excited states which accelerate the degradationprocess of the OLED.

The fundamental limiting factor to the triplet-singlet transition rateis a value of the parameter |H_(fi)/ΔE_(ST)|², where H_(fi) is thecoupling energy due to hyperfine or spin-orbit interactions, and ΔE_(ST)is the energetic splitting between singlet and triplet states.Traditional phosphorescent OLEDs rely on the mixing of singlet andtriplet states due to spin-orbital (SO) interaction, increasing H_(fi),and affording a lowest emissive state shared between a heavy metal atomand an organic ligand. This results in energy harvesting from all highersinglet and triplet states, followed by phosphorescence (relativelyshort-lived emission from the excited triplet). The shortened tripletlifetime reduces triplet exciton annihilation by charges and otherexcitons. Recent work by others suggests that the limit to theperformance of phosphorescent materials has been reached.

SUMMARY

The present disclosure relates to novel materials for OLEDs. In someembodiments, these OLEDs can reach higher excitation states withoutrapid degradation. It has now been discovered that thermally actuateddelayed fluorescence (TADF), which relies on minimization of ΔE_(ST) asopposed to maximization of H_(fi), can transfer population betweensinglet levels and triplet sublevels in a relevant timescale, such as,for example, 1 μs-10 ms. The compounds described herein are capable ofluminescing at higher energy excitation states than compounds previouslydescribed.

In some embodiments, the present disclosure provides compounds ofFormula (I):

wherein

R¹, R², R³, R⁴ and R⁵ are independently selected from hydrogen,deuterium, A¹, Ar¹, and D¹;

only one of R¹, R², R³, R⁴ and R⁵ is A¹;

at least one of R¹, R², R³, R⁴ and R⁵ is D¹;

A¹ is independently selected from CN, fluoroalkyl,

X^(A) is independently selected from O, S, and NR^(A)′;

R^(A) is independently selected from hydrogen, deuterium, halogen,cyano, substituted or unsubstituted alkyl, substituted or unsubstitutedalkoxy, substituted or unsubstituted aryl, substituted or unsubstitutedaryloxy, substituted or unsubstituted heteroaryl, substituted orunsubstituted heteroalyloxy, and silyl;

two or more instances of R^(A) taken together can form a ring system;

R^(A)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

-   -   two or more instances of R^(A)′ and R^(A) taken together can        form a ring system;

R^(A1) is fluoroalkyl;

L^(A) is independently selected from substituted or unsubstitutedarylene, and substituted or unsubstituted heteroarylene; wherein eachinstance of arylene and heteroarylene can be substituted with one ormore substituents independently selected from deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted aryl, and substitutedor unsubstituted heteroaryl; two or more of these substituents takentogether can form a ring system;

D¹ is independently selected from

X^(D) is independently selected from O, S, NR^(D)′, C(O), substituted orunsubstituted methylene, substituted or unsubstituted ethylene,substituted or unsubstituted vinylene, substituted or unsubstitutedo-arylene, and substituted or unsubstituted o-heteroarylene; whereineach instance of methylene, ethylene, vinylene, o-arylene oro-heteroarylene can be substituted with one or more substituentsindependently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl;

R^(D) is independently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted alkoxy, substituted orunsubstituted amino, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted heteroaryl,substituted or unsubstituted heteroaryloxy, and silyl,

two or more instances of R^(D) taken together can form a ring system;

R^(D)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

two or more instances of R^(D)′ and R^(D) taken together can form a ringsystem;

L^(D) is independently selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene;wherein each instance of arylene and heteroarylene can be substitutedwith one or more substituents independently selected from deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl; two or more of thesesubstituents taken together can form a ring system;

Ar¹ is independently selected from substituted or unsubstituted aryl andsubstituted or unsubstituted heteroaryl without containing any nitrogenatoms; and wherein each instance of aryl, and heteroaryl can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl withoutcontaining any nitrogen atoms; two or more of these substituents takentogether can form a ring system; and

-   -   each “*” represents a point of attachment to a carbon of the        pyridinyl center.

In some embodiments, the present disclosure provides compounds ofFormula (II):

wherein

A is selected from CN,

R¹, R² R³, R⁴, and R⁵ are independently selected from H, deuterium, Ph,and D;

D is independently selected from:

X is N or CR⁵:

Z is independently selected from H, Me, t-Bu, and heteroaryl: andheteroraryl is independently selected from

In some embodiments, the present disclosure provides compounds ofFormula (III):

wherein

A is selected from CN,

D is independently selected from H, Me, Ph,

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl,

3-30-membered heteroaryl, and diarylamino, and

at least one instance of D is selected from D1-D31,

In some embodiments, the present disclosure provides compounds ofFormula (IV):

wherein

A is selected from CN,

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph₂, O, N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino;

at least one instance of D is selected from D1-D31,

In some embodiments, the present disclosure provides compounds ofFormula (V):

wherein

A is selected from CN,

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one instance of D is selected from D1-D31.

In some embodiments, the present disclosure provides light emittingmaterials comprising compounds of Formula (I)-(V).

In some embodiments, the present disclosure provides delayed fluorescentemitters comprising the compound of Formula (I)-(V).

In some embodiments, the present disclosure provides organiclight-emitting diodes (OLED) comprising compounds of Formula (I)-(V).

In some embodiments, provided herein is an organic light-emitting diode(OLED) comprising an anode, a cathode, and at least one organic layercomprising a light emitting layer between the anode and the cathode,wherein the light emitting layer comprises:

a host material; and the compound of Formula (I)-(V).

In some embodiments, provided herein is an organic light-emitting diode(OLED) comprising an anode, a cathode, and at least one organic layercomprising a light emitting layer between the anode and the cathode,wherein the light emitting layer comprises:

a host material; and

a compound of Formula (I)-(V);

wherein the compound of formula (I)-(V) is a light emitting material.

In some embodiments, provided herein is an organic light-emitting diode(OLED) comprising an anode, a cathode, and at least one organic layercomprising a light emitting layer between the anode and the cathode,wherein the light emitting layer comprises:

a host material;

a compound of Formula (I)-(V); and

a light emitting material which is not a compound of Formula (I)-(V).

In some embodiments, provided herein is an organic light-emitting diode(OLED) comprising an anode, a cathode, and at least one organic layercomprising a light emitting layer between the anode and the cathode,wherein the light emitting layer comprises:

a compound of Formula(I)-(V);

a light emitting material which is not a compound of Formula (I)-(V).

In some embodiments, the compounds of Formula (I)-(V) are used in ascreen or a display.

In yet another aspect, the present disclosure relates to a method ofmanufacturing an OLED display, the method comprising:

forming a barrier layer on a base substrate of a mother panel;

forming a plurality of display units in units of cell panels on thebarrier layer;

forming an encapsulation layer on each of the display units of the cellpanels; and

applying an organic film to an interface portion between the cellpanels.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic wherein 1 denotes a substrate, 2 denotes an anode,3 denotes a hole injection layer, 4 denotes a hole transporting layer, 5denotes a light-emitting layer, 6 denotes an electron transportinglayer, and 7 denotes a cathode.

DETAILED DESCRIPTION

In one aspect, the present disclosure provides compounds of Formula (I):

wherein

R¹, R², R³, R⁴ and R⁵ are independently selected from hydrogen,deuterium, A¹, Ar¹, and D¹;

only one of R¹, R², R³, R⁴ and R⁵ is A¹,

at least one of R¹, R², R³, R⁴ and R⁵ is D¹;

A¹ is independently selected from CN, fluoroalkyl,

X^(A) is independently selected from O, S, and NR^(A)′;

R^(A) is independently selected from hydrogen, deuterium, halogen,cyano, substituted or unsubstituted alkyl, substituted or unsubstitutedalkoxy, substituted or unsubstituted aryl, substituted or unsubstitutedaryloxy, substituted or unsubstituted heteroaryl, substituted orunsubstituted heteroaryloxy, and silyl;

two or more instances of R^(A) taken together can form a ring system;

R^(A)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

two or more instances of R^(A)′ and R^(A) taken together can form a ringsystem;

R^(A1) is fluoroalkyl;

L^(A) is independently selected from substituted or unsubstitutedarylene, and substituted or unsubstituted heteroarylene; wherein eachinstance of arylene and heteroarylene can be substituted with one ormore substituents independently selected from deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted aryl, and substitutedor unsubstituted heteroaryl; two or more of these substituents takentogether can form a ring system;

D¹ is independently selected from

X^(D) is independently selected from O, S, NR^(D)′, C(O), substituted orunsubstituted methylene, substituted or unsubstituted ethylene,substituted or unsubstituted vinylene, substituted or unsubstitutedo-arylene, and substituted or unsubstituted o-heteroarylene; whereineach instance of methylene, ethylene, vinylene, o-arylene oro-heteroarylene can be substituted with one or more substituentsindependently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl;

R^(D) is independently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted alkoxy, substituted orunsubstituted amino, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted heteroaryl,substituted or unsubstituted heteroaryloxy, and silyl;

two or more instances of R^(D) taken together can form a ring system;

R^(D)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

-   -   two or more instances of R^(D)′ and R^(D) taken together can        form a ring system;

L^(D) is independently selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene;wherein each instance of arylene and heteroarylene can be substitutedwith one or more substituents independently selected from deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl; two or more of thesesubstituents taken together can form a ring system;

Ar¹ is independently selected from substituted or unsubstituted aryl andsubstituted or unsubstituted heteroaryl without containing any nitrogenatoms; and wherein each instance of aryl, and heteroaryl can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl withoutcontaining any nitrogen atoms; two or more of these substituents takentogether can form a ring system; and

-   -   each “*” represents a point of attachment to a carbon of the        pyridinyl center.

In one aspect, the present disclosure provides compounds of Formula(II):

wherein

A is selected from CN,

R¹, R², R³, R⁴, and R⁵ are independently selected from H, deuterium Ph,and D;

D is independently selected from:

X is N or CR⁵;

Z is independently selected from H, Me, t-Bu, and heteroaryl andheteroraryl is independently selected from

In one aspect, the present disclosure provides compounds of Formula(III):

wherein

A is selected from CN,

D is independently selected from H, Me, Ph,

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl,

3-30-membered heteroaryl, and diarylamino, and

at least one instance of D is selected from D1-D31,

In one aspect, the present disclosure provides compounds of Formula(IV):

wherein

A is selected from CN,

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one instance of D is selected from D1-D31.

In one aspect, the present disclosure provides compounds of Formula (V)

wherein

A is selected from CN,

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one instance of D is selected from D1-D31.

The examples are provided by way of explanation of the disclosure, andnot by way of limitation of the disclosure. In fact, it will be apparentto those skilled in the art that various modification and variations canbe made in the present disclosure without departing from the scope orspirit of the disclosure. For instance, features illustrated ordescribed as part of one embodiment can be used on another embodiment toyield a still further embodiment. Thus it is intended that the presentdisclosure cover such modifications and variations as come within thescope of the appended claims and their equivalents. Other objects,features, and aspects of the present disclosure are disclosed in, or canbe derived from, the following detailed description. It is to beunderstood by one of ordinary skill in the art that the presentdiscussion is a description of exemplary embodiments only, and is not tobe construed as limiting the broader aspects of the present disclosure.

Definitions

Unless otherwise defined herein, scientific and technical terms used inthis application shall have the meanings that are commonly understood bythose of ordinary skill in the art. Generally, nomenclature used inconnection with, and techniques of, chemistry described herein, arethose well-known and commonly used in the art.

The term “acyl” is art-recognized and refers to a group represented bythe general formula hydrocarbylC(O)—, preferably alkylC(O)—.

The term “acylamino” is art-recognized and refers to an amino groupsubstituted with an acyl group and may be represented, for example, bythe formula hydrocarbylC(O)NH—.

The term “acyloxy” is art-recognized and refers to a group representedby the general formula hydrocarbylC(O)O—, preferably alkylC(O)O—.

The term “alkoxy” refers to an alkyl group, having an oxygen attachedthereto. In some embodiments, an alkoxy has 1-20 carbon. In someembodiments, an alkoxy has 1-12 carbon atoms. Representative alkoxygroups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxyand the like.

The term “alkoxyalkyl” refers to an alkyl group substituted with analkoxy group and may be represented by the general formulaalkyl-O-alkyl.

The term “alkenyl”, as used herein, refers to an aliphatic groupcomprising at least one double bond and is intended to include both“unsubstituted alkenyls” and “substituted alkenyls”, the latter of whichrefers to alkenyl moieties having substituents replacing a hydrogen onone or more carbons of the alkenyl group. Typically, a straight chainedor branched alkenyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 12 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more double bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed below,except where stability is prohibitive. For example, substitution ofalkenyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl groups is contemplated.

An “alkyl” group or “alkane” is a straight chained or branchednon-aromatic hydrocarbon which is completely saturated. Typically, astraight chained or branched alkyl group has from 1 to about 20 carbonatoms, preferably from 1 to about 12 unless otherwise defined. In someembodiments, the alkyl group has from 1 to 8 carbon atoms, from 1 to 6carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3 carbon atoms.Examples of straight chained and branched alkyl groups include methyl,ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, pentyl,hexyl, pentyl and octyl.

Moreover, the term “alkyl” as used throughout the specification,examples, and claims is intended to include both “unsubstituted alkyls”and “substituted alkyls”, the latter of which refers to alkyl moietieshaving substituents replacing a hydrogen on one or more substitutablecarbons of the hydrocarbon backbone. Such substituents, if not otherwisespecified, can include, for example, a halogen (e.g., fluoro), ahydroxyl, a carbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl,or an acyl), a thiocarbonyl (such as a thioester, a thioacetate, or athioformate), an alkoxy, a phosphoryl, a phosphate, a phosphonate, aphosphinate, an amino, an amido, an amidine, an imine, a cyano, a nitro,an azido, a sulfhydryl, an alkylthio, a sulfate, a sulfonate, asulfamoyl, a sulfonamido, a sulfonyl, a heterocyclyl, an aralkyl, or anaromatic or heteroaromatic moiety. In preferred embodiments, thesubstituents on substituted alkyls are selected from C₁₋₆ alkyl, C₃₋₆cycloalkyl, halogen, carbonyl, cyano, or hydroxyl. In more preferredembodiments, the substituents on substituted alkyls are selected fromfluoro, carbonyl, cyano, or hydroxyl. It will be understood by thoseskilled in the art that the moieties substituted on the hydrocarbonchain can themselves be substituted, if appropriate. For instance, thesubstituents of a substituted alkyl may include substituted andunsubstituted forms of amino, azido, imino, amido, phosphoryl (includingphosphonate and phosphinate), sulfonyl (including sulfate, sulfonamido,sulfamoyl and sulfonate), and silyl groups, as well as ethers,alkylthios, carbonyls (including ketones, aldehydes, carboxylates, andesters), —CF₃, —CN and the like. Exemplary substituted alkyls aredescribed below. Cycloalkyls can be further substituted with alkyls,alkenyls, alkoxys, alkylthios, aminoalkyls, carbonyl-substituted alkyls,—CF₃, —CN, and the like.

The term “C_(x-y)” when used in conjunction with a chemical moiety, suchas, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups that contain from x to y carbons in the chain. Forexample, the term “C_(x-y) alkyl” refers to substituted or unsubstitutedsaturated hydrocarbon groups, including straight-chain alkyl andbranched-chain alkyl groups that contain from x to y carbons in thechain, including haloalkyl groups. Preferred haloalkyl groups includetrifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, andpentafluoroethyl. C₀ alkyl indicates a hydrogen where the group is in aterminal position, a bond if internal. The terms “C_(2-y) alkenyl” and“C_(2-y) alkynyl” refer to substituted or unsubstituted unsaturatedaliphatic groups analogous in length and possible substitution to thealkyls described above, but that contain at least one double or triplebond respectively.

The term “alkylamino”, as used herein, refers to an amino groupsubstituted with at least one alkyl group.

The term “alkylthio”, as used herein, refers to a thiol groupsubstituted with an alkyl group and may be represented by the generalformula alkylS—. The term “arylthio”, as used herein, refers to a thiolgroup substituted with an alkyl group and may be represented by thegeneral formula arylS—.

The term “alkynyl”, as used herein, refers to an aliphatic groupcomprising at least one triple bond and is intended to include both“unsubstituted alkynyls” and “substituted alkynyls”, the latter of whichrefers to alkynyl moieties having substituents replacing a hydrogen onone or more carbons of the alkynyl group. Typically, a straight chainedor branched alkynyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 10 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more triple bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed above,except where stability is prohibitive. For example, substitution ofalkynyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl groups is contemplated.

The term “amide”, as used herein, refers to a group

wherein each R^(A) independently represent a hydrogen or hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The terms “amine” and “amino” are art-recognized and refer to bothunsubstituted and substituted amines and salts thereof, e.g., a moietythat can be represented by

wherein each R^(A) independently represents a hydrogen or a hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The term “aminoalkyl”, as used herein, refers to an alkyl groupsubstituted with an amino group.

The term “aralkyl”, as used herein, refers to an alkyl group substitutedwith an aryl group.

The term “aryl” as used herein include substituted or unsubstitutedsingle-ring aromatic groups in which each atom of the ring is carbon.Preferably the ring is a 6- or 20-membered ring, more preferably a6-membered ring. Preferably an aryl has 6-40 carbon atoms, morepreferably has 6-25 carbon atoms. The term “aryl” also includespolycyclic ring systems having two or more cyclic rings in which two ormore carbons are common to two adjoining rings wherein at least one ofthe rings is aromatic, e.g., the other cyclic rings can be cycloalkyls,cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.Aryl groups include benzene, naphthalene, phenanthrene, phenol, aniline,and the like.

The term “carbamate” is art-recognized and refers to a group

wherein each R^(A) independently represent hydrogen or a hydrocarbylgroup, such as an alkyl group, or both R^(A) taken together with theintervening atom(s) complete a heterocycle having from 4 to 8 atoms inthe ring structure.

The terms “carbocycle”, and “carbocyclic”, as used herein, refers to asaturated or unsaturated ring in which each atom of the ring is carbon.Preferably, a carbocylic group has from 3 to 20 carbon atoms. The termcarbocycle includes both aromatic carbocycles and non-aromaticcarbocycles. Non-aromatic carbocycles include both cycloalkane rings, inwhich all carbon atoms are saturated, and cycloalkene rings, whichcontain at least one double bond. “Carbocycle” includes 5-7 memberedmonocyclic and 8-12 membered bicyclic rings. Each ring of a bicycliccarbocycle may be selected from saturated, unsaturated and aromaticrings. Carbocycle includes bicyclic molecules in which one, two or threeor more atoms are shared between the two rings. The term “fusedcarbocycle” refers to a bicyclic carbocycle in which each of the ringsshares two adjacent atoms with the other ring. Each ring of a fusedcarbocycle may be selected from saturated, unsaturated and aromaticrings. In an exemplary embodiment, an aromatic ring, e.g., phenyl (Ph),may be fused to a saturated or unsaturated ring, e.g, cyclohexane,cyclopentane, or cyclohexene. Any combination of saturated, unsaturatedand aromatic bicyclic rings, as valence permits, is included in thedefinition of carbocyclic. Exemplary “carbocycles” include cyclopentane,cyclohexane, bicyclo[2.2.1]heptane, 1,5-cyclooctadiene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]oct-3-ene, naphthalene andadamantane. Exemplary fused carbocycles include decalin, naphthalene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]octane,4,5,6,7-tetrahydro-1H-indene and bicyclo[4.1,0]hept-3-ene. “Carbocycles”may be sushstituted at any one or more positions capable of bearing ahydrogen atom.

A “cycloalkyl” group is a cyclic hydrocarbon which is completelysaturated. “Cycloalkyl” includes monocyclic and bicyclic rings.Preferably, a cycloalkyl group has from 3 to 20 carbon atoms. Typically,a monocyclic cycloalkyl group has from 3 to about 10 carbon atoms, moretypically 3 to 8 carbon atoms unless otherwise defined. The second ringof a bicyclic cycloalkyl may be selected from saturated, unsaturated andaromatic rings. Cycloalkyl includes bicyclic molecules in which one, twoor three or more atoms are shared between the two rings. The term “fusedcycloalkyl” refers to a bicyclic cycloalkyl in which each of the ringsshares two adjacent atoms with the other ring. The second ring of afused bicyclic cycloalkyl may be selected from saturated, unsaturatedand aromatic rings. A “cycloalkenyl” group is a cyclic hydrocarboncomprising one or more double bonds.

The term “carbocyclylalkyl”, as used herein, refers to an alkyl groupsubstituted with a carbocycle group.

The term “carbonate”, as used herein, refers to a group —OCO₂—R^(A),wherein R^(A) represents a hydrocarbyl group.

The term “carboxy”, as used herein, refers to a group represented by theformula —CO₂H.

The term “ester”, as used herein, refers to a group —C(O)OR^(A) whereinR^(A) represents a hydrocarbyl group.

The term “ether”, as used herein, refers to a hydrocarbyl group linkedthrough an oxygen to another hydrocarbyl group, Accordingly, an ethersubstituent of a hydrocarbyl group may be hydrocarbyl-O—. Ethers may beeither symmetrical or unsymmetrical. Examples of ethers include, but arenot limited to, heterocycle-O-heterocycle and aryl-O-heterocycle. Ethersinclude “alkoxyalkyl” groups, which may be represented by the generalformula alkyl-O-alkyl.

The terms “halo” and “halogen” as used herein means halogen and includeschloro, fluoro, bromo, and iodo.

The terms “hetaralkyl” and “heteroaralkyl”, as used herein, refers to analkyl group substituted with a hetaryl group.

The term “heteroalkyl”, as used herein, refers to a saturated orunsaturated chain of carbon atoms and at least one heteroatom, whereinno two heteroatoms are adjacent.

The terms “heteroatyl” and “hetaryl” include substituted orunsubstituted aromatic single ring structures, preferably 5- to20-membered rings, more preferably 5- to 6-membered rings, whose ringstructures include at least one heteroatom, preferably one to fourheteroatoms, more preferably one or two heteroatoms. Preferably aheteroaryl has 2-40 carbon atoms, more preferably has 2-25 carbon atoms.The terms “heteroaryl” and “hetaryl” also include polycyclic ringsystems having two or more cyclic rings in which two or more carbons arecommon to two adjoining rings wherein at least one of the rings isheteroaromatic, e.g., the other cyclic rings can be cycloalkyls,cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls,Heteroaryl groups include, for example, pyrrole, furan, thiophene,imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine, pyridazine,pyrimidine, and carbazole, and the like.

The term “aryloxy” refers to an aryl group, having an oxygen attachedthereto. Preferably an aryloxy has 6-40 carbon atoms, more preferablyhas 6-25 carbon atoms.

The term “heteroaryloxy” refers to an aryl group, having an oxygenattached thereto. Preferably a heteroaryloxy has 2-40 carbon atoms, morepreferably has 2-25 carbon atoms.

The term “heteroatom” as used herein means an atom of any element otherthan carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, andsulfur.

The terms “heterocyclyl”, “heterocycle”, and “heterocyclic” refer tosubstituted or unsubstituted non-aromatic ring structures, preferably 3-to 20-membered rings, more preferably 3- to 7-membered rings, whose ringstructures include at least one heteroatom, preferably one to fourheteroatoms, more preferably one or two heteroatoms. The terms“heterocyclyl” and “heterocyclic” also include polycyclic ring systemshaving two or more cyclic rings in which two or more carbons are commonto two adjoining rings wherein at least one of the rings isheterocyclic, e.g., the other cyclic rings can be cycloalkyls,cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.Heterocyclyl groups include, for example, piperidine, piperazine,pyrrolidine, morpholine, lactones, lactams, and the like.

The term “heterocyclylalkyl”, as used herein, refers to an alkyl groupsubstituted with a heterocycle group.

The term “hydrocarbyl”, as used herein, refers to a group that is bondedthrough a carbon atom, wherein that carbon atom does not have a ═O or ═Ssubstituent. Hydrocarbyls may optionally include heteroatoms.Hydrocarbyl groups include, but are not limited to, alkyl, alkenyl,alkynyl, alkoxyalkyl, aminoalkyl, aralkyl, aryl, aralkyl, carbocyclyl,cycloalkyl, carbocyclylalkyl, heteroaralkyl, heteroaryl groups bondedthrough a carbon atom, heterocyclyl groups bonded through a carbon atom,heterocyclylakyl, or hydroxyalkyl. Thus, groups like methyl,ethoxyethyl, 2-pyridyl, and trifluoromethyl are hydrocarbyl groups, butsubstituents such as acetyl (which has a ═O substituent on the linkingcarbon) and ethoxy (which is linked through oxygen, not carbon) are not.

The term “hydroxyalkyl”, as used herein, refers to an alkyl groupsubstituted with a hydroxy group.

The term “lower” when used in conjunction with a chemical moiety, suchas, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups where there are six or fewer non-hydrogen atoms in thesubstituent. A “lower alkyl”, for example, refers to an alkyl group thatcontains six or fewer carbon atoms. In some embodiments, the alkyl grouphas from 1 to 6 carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3carbon atoms. In certain embodiments, acyl, acyloxy, alkyl, alkenyl,alkynyl, or alkoxy substituents defined herein are respectively loweracyl, lower acyloxy, lower alkyl, lower alkenyl, lower alkynyl, or loweralkoxy, whether they appear alone or in combination with othersubstituents, such as in the recitations hydroxyalkyl and aralkyl (inwhich case, for example, the atoms within the aryl group are not countedwhen counting the carbon atoms in the alkyl substituent).

The terms “polycyclyl”, “polycycle”, and “polycyclic” refer to two ormore rings (e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls,heteroaryls, and/or heterocyclyls) in which two or more atoms are commonto two adjoining rings, e.g., the rings are “fused rings”. Each of therings of the polycycle can be substituted or unsubstituted. In certainembodiments, each ring of the polycycle contains from 3 to 10 atoms inthe ring, preferably from 5 to 7.

In the phrase “poly(meta-phenylene oxides)”, the term “phenylene” refersinclusively to 6-membered aryl or 6-membered heteroaryl moieties.Exemplary poly(meta-phenylene oxides) are described in the first throughtwentieth aspects of the present disclosure.

The term “silyl” refers to a silicon moiety with three hydrocarbylmoieties attached thereto.

The term “substituted” refers to moieties having substituents replacinga hydrogen on one or more carbons of the backbone. It will be understoodthat “substitution” or “substituted with” includes the implicit provisothat such substitution is in accordance with permitted valence of thesubstituted atom and the substituent, and that the substitution resultsin a stable compound, e.g., which does not spontaneously undergotransformation such as by rearrangement, cyclization, elimination, etc.Moieties that may be substituted can include any appropriatesubstituents described herein, for example, acyl, acylamino, acyloxy,alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio,alkynyl, amide, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl,cycloalkyl, carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl,heterocyclyl, heterocyclylalkyl, hydrocarbyl, silyl, sulfone, orthioether. As used herein, the term “substituted” is contemplated toinclude all permissible substituents of organic compounds. In a broadaspect, the permissible substituents include acyclic and cyclic,branched and unbranched, carbocyclic and heterocyclic, aromatic andnon-aromatic substituents of organic compounds. The permissiblesubstituents can be one or more and the same or different forappropriate organic compounds. For purposes of this invention, theheteroatoms such as nitrogen may have hydrogen and/or any permissiblesubstituents of organic compounds described herein which satisfy thevalences of the heteroatoms. Substituents can include any substituentsdescribed herein, for example, a halogen, a hydroxyl, a carbonyl (suchas a carboxyl, an alkoxycarbonyl, a formyl, or an acyl), a thiocarbonyl(such as a thioester, a thioacetate, or a thioformate), an alkoxy, aphosphoryl, a phosphate, a phosphonate, a phosphinate, an amino, anamido, an amidine, an imine, a cyano, a nitro, an azido, a sulfhydryl,an alkylthio, a sulfate, a sulfonate, a sulfamoyl, a sulfonamido, asulfonyl, a heterocyclyl, an aralkyl, or an aromatic or heteroaromaticmoiety. In preferred embodiments, the substituents on substituted alkylsare selected from C₁₋₆ alkyl, C₃₋₆ cycloalkyl, halogen, carbonyl, cyano,or hydroxyl. In more preferred embodiments, the substituents onsubstituted alkyls are selected from fluoro, carbonyl, cyano, hydroxyl.It will be understood by those skilled in the art that substituents canthemselves be substituted, if appropriate. Unless specifically stated as“unsubstituted,” references to chemical moieties herein are understoodto include substituted variants. For example, reference to an “aryl”group or moiety implicitly includes both substituted and unsubstitutedvariants.

The term “sulfonate” is art-recognized and refers o the group SO₃H, or apharmaceutically acceptable salt thereof.

The term “sulfone” is art-recognized and refers to the group—S(O)₂—R^(A), wherein R^(A) represents a hydrocarbyl.

The term “thioether”, as used herein, is equivalent to an ether, whereinthe oxygen is replaced with a sulfur.

The term “symmetrical molecule,” as used heroin, refers to moleculesthat are group symmetric or synthetic symmetric. The term “groupsymmetric,” as used herein, refers to molecules that have symmetryaccording to the group theory of molecular symmetry. The term “syntheticsymmetric,” as used herein, refers to molecules that are selected suchthat no regioselective synthetic strategy is required.

The term “donor,” as used herein, refers to a molecular fragment thatcan be used in organic light emitting diodes and is likely to donateelectrons from its highest occupied molecular orbital to an acceptorupon excitation. In preferred embodiments, donors contain substitutedamino groups. In an example embodiment, donors have an ionizationpotential greater than or equal to −6.5 eV.

The term “acceptor,” as used herein, refers to a molecular fragment thatcan be used in organic light emitting diodes and is likely to acceptelectrons into its lowest unoccupied molecular orbital from a donor thathas been subject to excitation. In an example embodiment, acceptors havean electron affinity loss than or equal to −0.5 eV.

The term “linker,” or “bridge,” as used herein, refers to a molecularfragment that can be included in a molecule which is covalently linkedbetween acceptor and donor moieties. The linker can, for example, befurther conjugated to the acceptor moiety, the donor moiety, or both.Without being bound to any particular theory, it is believed that thelinker moiety can sterically restrict the acceptor and donor moietiesinto a specific configuration, thereby preventing the overlap betweenthe conjugated a system of donor and acceptor moieties. Examples ofsuitable linker moieties include phenyl, ethenyl, and ethynyl.

The term “multivalent,” as used herein, refers to a molecular fragmentthat is connected to at least two other molecular fragments. Forexample, a linker moiety, is multivalent.

“

” or “*” as used herein, refers to a point of attachment between twoatoms.

“Hole transport layer (HTL)” and like terms mean a layer made from amaterial which transports holes. High hole mobility is recommended. TheHTL is used to help block passage of electrons transported by theemitting layer. Low electron affinity is typically required to blockelectrons. The HTL should desirably have larger triplets to blockexcitor migrations from an adjacent emisse layer (EML). Examples of HTLcompounds include, but are not limited to,di(p-tolyl)aminophenyl]cyclohexane (TAPC),N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD), andN,N′-diphenyl-N,N′-bis(1-naphthyl)-(1,1′-biphenyl)-4,4′-diamine (NPB,α-NPD).

“Emitting layer” and like terms mean a layer which emits light. In someembodiments, the emitting layer comprises host material and guestmaterial. The guest material can also be referred to as a dopantmaterial, but the disclosure, is not limited there to. The host materialor “host” could be bipolar or unipolar, and may be used alone or bycombination of two or more host materials. The opto-electricalproperties of the host material may differ to which type of guestmaterial (TADF, Phosphorescent or Fluorescent) is used. For Fluorescentguest materials, the host materials should have good spectral overlapbetween absorption of the guest material and emission of the material toinduce good Förster transfer to guest materials. For Phosphorescentguest materials, the host materials should have high triplet energy toconfine triplets of the guest material. For TADF guest materials, thehost materials should have both spectral overlap and higher tripletenergy.

“Dopant” and like terms, refer to additive materials for carriertransporting layers, emitting layers or other layers. In carriertransporting layers, dopant and like terms perform as an electronacceptor or a donator that increases the conductivity of an organiclayer of an organic electronic device, when added to the organic layeras an additive. Organic semiconductors may likewise be influenced, withregard to their electrical conductivity, by doping. Such organicsemiconducting matrix materials may be made up either of compounds withelectron-donor properties or of compounds with electron -acceptorproperties. In emitting layers, dopant and like terms also mean thelight emitting material which is dispersed in a matrix, for example, ahost. When a triplet harvesting material is doped into an emitting layeror contained in an adjacent layer so as to improve exciton generationefficiency, it is named as assistant dopant. The content of theassistant dopant in the light emitting layer or the adjacent layer isnot particularly limited so as the triplet harvesting material improvesthe exciton generation efficiency. The content of the assistant dopantin the light emitting layer is preferably higher than, more preferablyat least twice than the light emitting material. In the light emittinglayer, the content of the host material is preferably 50% by weight ormore, the content of the assistant dopant is preferably from 5% byweight to less than 50% by weight, and the content of the light emittingmaterial is preferably more than 0% b weight to less than 25% by weight,more preferably from 0% by weight to less than 10% by weight. Thecontent of the assitant dopant in the adjecent layer may be more than50% by weight and may be 100% by weight. In the case where a devicecontaining a triplet harvesting material in a light emitting layer or anadjecent layer has a higher light emission efficiency than a devicewithout the triplet harvesting material, such triplet harvestingmaterial ffinctions as an assistant dopant. A light emitting layercontaining a host material, an assistant dopant and a light emittingmaterial satisfies the following (A) and preferably satisfies thefollowing B:

ES1(A)>ES1(B)>ES1(C)   (A)

ET1(A)>ET1(B)   (B)

wherein ES1(A) represents a lowest excited singlet energy level of thehost material; ES1(B) represents a lowest excited singlet energy levelof the assistant dopant ES1(C) represents a lowest excited singletenergy level of the light emitting material; ET1(A) represents a lowestexcited triplet energy level at 77 K of the host material; and ET1(B)represents a lowest excited triplet energy level at 77 K of theassistant dopant. The assistant dopant has an energy difference ΔEstbetween a lowest singlet excited state and a lowest triplet excitedstate at 77 K of preferably 0.3 eV or less, more preferably 0.2 eV orless, still more preferably 0.1 eV or less.

In the compounds of this invention any atom not specifically designatedas a particular isotope is meant to represent any stable isotope of thatatom. Unless otherwise stated, when a position is designatedspecifically as “H” or “hydrogen”, the position is understood to havehydrogen at its natural abundance isotopic composition. Also unlessotherwise stated, when a position is designated specifically as “D” or“deuterium”, the position is understood to have deuterium at anabundance that is at least 3340 times greater than the natural abundanceof deuterium, which is 0.015% (i.e., at least 50.1% incorporation ofdeuterium).

“D” and “d” both refer to deuterium.

“Substituted with deuterium” refers to the replacement of one or morehydrogen atoms with a corresponding number of deuterium atoms.

The term “isotopic enrichment factor” as used herein means the ratiobetween the isotopic abundance and the natural abundance of a specifiedisotope.

In various embodiments, compounds of this mention have an isotopicenrichment factor for each designated deuterium atom of at least 3500(52.5% deuterium incorporation at each designated deuterium atom), atleast 4000 (60% deuterium incorporation), at least 4500 (67.5% deuteriumincorporation), at least 5000 (75% deuterium), at least 5500 (82.5%deuterium incorporation), at least 6000 (90% deuterium incorporation),at least 6333.3 (95% deuterium incorporation), at least 6466.7 (97%deuterium incorporation), at least 6600 (99% deuterium incorporation),or at least 6633.3 (99.5% deuterium incorporation).

The term “isolopologue” refers to a species that differs from a specificcompound of this invention only in the isotopic composition thereof.

The term “compound,” when referring to a compound of this invention,refers to a collection of molecules having an identical chemicalstructure, except that there may be isotopic variation among theconstituent atoms of the molecules. Thus, it will be clear to those ofskill in the art that a compound represented by a particular chemicalstructure containing indicated deuterium atoms, will also contain lesseramounts of isotopologues having hydrogen atoms at one or more of thedesignated deuterium positions in that structure. The relative amount ofsuch isotopologues in a compound of this invention will depend upon anumber of factors including the isotopic purity of deuterated reagentsused to make the compound and the efficiency of incorporation ofdeuterium in the various synthesis steps used to prepare the compound.However, as set forth above the relative amount of such isotopologues intoto will be less than 49.9% of the compound. In other embodiments, therelative amount of such isotopologues in toto will be less than 47.5%,less than 40%, less than 32.5%, less than 25%, less than 17.5%, lessthan 10%, less than 5%, less than 3%, less than 1%, or less than 0.5% ofthe compound.

Principles of OLED

OLEDs are typically composed of a layer of organic materials orcompounds between two electrodes, an anode and a cathode. The organicmolecules are electrically conductive as a result of delocalization of πelectronics caused by conjugation over part or all of the molecule. Whenvoltage is applied, electrons from the highest occupied molecularorbital (HOMO) present at the anode flow into the lowest unoccupiedmolecular orbital (LUMO) of the organic molecules present at thecathode. Removal of electrons from the HOMO is also referred to asinserting electron holes into the HOMO. Electrostatic forces bring theelectrons and the holes towards each other until they recombine and forman exciton (which is the bound state of the electron and the hole). Asthe excited state decays and the energy levels of the electrons relax,radiation having a frequency in the visible spectrum is emitted. Thefrequency of this radiation depends on the band gap of the material,which is the difference in energy between the HOMO and the LUMO.

As electrons and holes are fermions with half integer spin, an excitormay either be in a singlet state or a triplet state depending on how thespins of the electron and hole have been combined. Statistically, threetriplet excitors will be formed for each singlet exciton. Decay fromtriplet states is spin forbidden, which results in increases in thetimescale of the transition and limits the internal efficiency offluorescent devices. Phosphorescent organic light-emitting diodes makeuse of spin-orbit interactions to facilitate intersystem crossingbetween singlet and triplet states, thus obtaining emission from bothsinglet and triplet states and improving the internal efficiency.

One prototypical phosphorescent material is iridiumtris(2-phenylpyridine) (Ir(ppy)₃) in which the excited state is a chargetransfer from the Ir atom to the organic ligand. Such approaches havereduced the triplet lifetime to about several several orders ofmagnitude slower than the radiative lifetimes of fully-allowedtransitions such as fluorescence. Ir-based phosphors have proven to beacceptable for many display applications, but losses due to largetriplet densities still prevent the application of OLEDs to solid-statelighting at higher brightness.

TADF seeks to minimize ΔE_(ST). The reduction in exchange splitting fromtypical values of 0.4-0.7 eV to a gap of the order of the thermal energy(proportional to kBT, where kB represents the Boltzmann constant, and Trepresents temperature) means that thermal agitation can transferpopulation between singlet levels and triplet sublevels in a relevanttimescale even if the coupling between states is small.

TADF molecules consist of donor and acceptor moieties connected directlyby a covalent bond or via a conjugated linker (or “bridge”). A “donor”moiety is likely to transfer electrons from its HOMO upon excitation tothe “acceptor” moiety. An “acceptor” moiety is likely to accept theelectrons from the “donor” moiety into its LUMO. The donor-acceptornature of TADF molecules results in low-lying excited states withcharge-transfer character that exhibit very low ΔE_(ST). Since thermalmolecular motions can randomly vary the optical properties ofdonor-acceptor systems, a rigid three-dimensional arrangement of donorand acceptor moieties can be used to limit the non-radiative decay ofthe charge-transfer state by internal conversion during the lifetime ofthe excitation.

It is beneficial, therefore, to decrease ΔE_(ST), and to create a systemwith increased reversed intersystem crossing (RISC) capable ofexploiting triplet excitons. Such a system, it is believed, will resultin increased quantum efficiency and decreased emission lifetimes.Systems with these features will be capable of emitting light withoutbeing subject to the rapid degradation prevalent in OLEDs known today.

Compounds of the Disclosure

In some embodiments, the compounds have a structure of Formula (I):

wherein

R¹, R², R³, R⁴ and R⁵ are independently selected from hydrogen,deuterium, A¹, Ar¹, and D¹;

only one of R¹, R², R³, R⁴ and R⁵ is A¹;

at least one of R¹, R², R³, R⁴ and R⁵ is D¹;

A¹ is independently selected from CN, fluoroalkyl,

X^(A) is independently selected from O, S, and NR^(A)′;

R^(A) is independently selected from hydrogen, deuterium, halogen,cyano, substituted or unsubstituted alkyl, substituted or unsubstitutedalkoxy, substituted or unsubstituted aryl, substituted or unsubstitutedaryloxy, substituted or unsubstituted heteroaryl, substituted orunsubstituted heteroaryloxy, and silyl;

two or more instances of R^(A) taken together can form a ring system;

R^(A)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

-   -   two or more instances of R^(A)′ and R^(A) taken together can        form a ring system;

R^(A1) is fluoroalkyl;

L^(A) is independently selected from substituted or unsubstitutedarylene, and substituted or unsubstituted heteroarylene; wherein eachinstance of arylene and heteroarylene can be substituted with one ormore substituents independently selected from deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted aryl, and substitutedor unsubstituted heteroaryl; two or more of these substituents takentogether can form a ring system;

D¹ is independently selected from

X^(D) is independently selected from O, S, NR^(D)′, C(O), substituted orunsubstituted methylene, substituted or unsubstituted ethylene,substituted or unsubstituted vinylene, substituted or unsubstitutedo-arylene, and substituted or unsubstituted o-heteroarylene; whereineach instance of methylene, ethylene, vinylene, o-arylene oro-heteroarylene can be substituted with one or more substituentsindependently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl;

R^(D) is independently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted alkoxy, substituted orunsubstituted amino, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted heteroaryl,substituted or unsubstituted heteroaryloxy, and silyl;

two or more instances of R^(D) taken together can form a ring system;

R^(D)′ is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, andsubstituted or unsubstituted heteroaryl;

-   -   two or more instances of R^(D)′ and R^(D) taken together can        form a ring system;

L^(D) is independently selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene;wherein each instance of arylene and heteroarylene can be substitutedwith one or more substituents independently selected from deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl, two or more of thesesubstituents taken together can form a ring system;

Ar¹ is independently selected from substituted or unsubstituted aryl andsubstituted or unsubstituted heteroaryl without containing any nitrogenatoms; and wherein each instance of aryl, and heteroaryl can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted substituted or unsubstitutedaryl, and substituted or unsubstituted heteroaryl without containing anynitrogen atoms; two or more of these substituents taken together canform a ring system; and

-   -   each “*” represents a point of attachment to a carbon of the        pyridinyl center.

In some embodiments, alkyl is C1-C20 alkyl. In some embodiments, alkylis C1-C12 alkyl. In some embodiments, alkyl is C1-C8 alkyl. In someembodiments, alkyl is C1-C4 alkyl.

In some embodiments, aryl is C6-C40 aryl. In some embodiments, and isC6-C25 aryl. In some embodiments, aryl is C6-C20 aryl, In someembodiments, aryl is C6-C12 aryl.

In some embodiments, heteroaryl is C2-C40 heteroaryl. In someembodiments, heteroaryl is C6-C25 heteroaryl. In some embodiments,heteroaryl is C6-C20 heteroaryl. In some embodiments, heteroaryl isC6-C12 heteroaryl.

In some embodiments, alkoxy is C1-C20 alkoxy. In some embodiments,alkoxy is C1-C12 alkoxy. In some embodiments, alkoxy is C1-C8 alkoxy. Insome embodiments, alkoxy is C1-C4 alkoxy.

In some embodiments, aryloxy is C6-C40 aryloxy. In some embodiments,aryloxy is C6-C25 aryloxy. In some embodiments, aryloxy is C6-C20aryloxy. In some embodiments, aryloxy is C6-C12 aryloxy.

In some embodiments, heteroaryloxy is C2-C40 heteroaryloxy. In someembodiments, heteroaryloxy is C2-C25 heteroaryloxy. In some embodiments,heteroaryloxy is C2-C20 heteroaryloxy. In some embodiments,heteroaryloxy is C2-C12 heteroaryloxy.

In some embodiments, A¹ is selected from

In some embodiments, A¹ is selected from

In some embodiments, wherein A¹ is

CN-L^(A)_*.

In some embodiments, A¹ is

R^(A1)-L^(A)-*.

In some embodiments, R¹ is A¹.

In some embodiments, R² is A¹.

In some embodiments, R³ is A¹.

In some embodiments, if R² is A¹, at least one instance of R¹ and R³ isnot H.

In some embodiments, if R³ is A¹, at least one instance of R² and R⁴ isnot H.

In some embodiments, four of R¹, R², R³, R⁴, or R⁵ are not H.

In some embodiments, none of R¹, R², R³, R⁴, and R⁵ are H.

In some embodiments, D¹ is

In some embodiments, D¹ is

In some embodiments, D¹ is

In some embodiments, L^(D) is a single bond.

In some embodiments, L^(A) is a substituted or unsubstituted arylene.

In some embodiments, Ar¹ is independently selected from

-   -   In some embodiments, Ar¹ is independently selected from        substituted or unsubstituted phenyl, substituted or        unsubstituted biphenylenyl, and substituted or unsubstituted        terphenylenyl.

In some embodiments, the compound is selected from:

In some embodiments, the compound is selected from:

In some embodiments, the compound is

In some embodiments, the compound is selected from:

In some embodiments, the compound is

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments e compound of Formula (I) selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments e compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments e compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments e compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments the compound of Formula (I) is selected from

In some embodiments the compound of Formula (I) selected from

In some embodiments e compound of Formula (I) selected from

In some embodiments, the compounds have a structure of Formula (II):

wherein

A is selected from CN,

R¹, R² R³, R⁴, and R⁵ are independently selected from H, deuterium Ph,and D;

D is independently selected from:

X is N or CR⁵;

Z is independently selected from H, Me, t-Bu, and heteroaryl, andheteroraryl is independently selected from

In some embodiments, A is A1. In some embodiments, A is A2. In someembodiments, A is A3. In some embodiments, A is A4. In some embodiments,A is A5. In some embodiments, A is A6. In some embodiments, A is A7. Insome embodiments. A is A8. In some embodiments, A is A9. In someembodiments, A is A10. In some embodiments, A is A11. In someembodiments, A is A12. In some embodiments, A is A13.

In some embodiments, A is selected from A1, A2, A3, and A4. In someembodiments, A is selected from A5, A6, A7, and A8. In some embodiments,A is selected from A9, A10, A11, A12, and A13.

In some embodiments, X is N. In come embodiments, X is CR⁵.

In some embodiments, R¹ is H. In some embodiments, R¹ is Ph. In someembodiments, R¹ is d. In some embodiments, R¹ is D.

In some embodiments, R² is H. In some embodiments, R² is Ph. In someembodiments. R² is d. In some embodiments, R² is D.

In some embodiments, R³ is H. In some embodiments, R³ is Ph. In someembodiments. R³ is d. In some embodiments, R³ is D.

In some embodiments, R⁴ is H. In some embodiments, R⁴ is Ph. In someembodiments, R⁴ is d. In some embodiments, R⁴ is D.

In some embodiments, R⁵ is H. In some embodiments, R⁵ is Ph. In someembodiments. R⁵ is d. In some embodiments, R⁵ is D.

In some embodiments, D is D 1. In some embodiments, D is D2. In someembodiments, D is D3. In some embodiments, D is D4. In some embodiments,D is D5. In some embodiments, D is D6. In some embodiments, D is D7. Insome embodiments, D is D8. In some embodiments, D is D9. In someembodiments, D is D10. In some embodiments, D is D11. In someembodiments, D is D12. In some embodiments, D is D13. In someembodiments, D is D14. in some embodiments, D is D15. In someembodiments, D is D16. In some embodiments, D is D17, In someembodiments, D is D18. In some embodiments, D is D19. In someembodiments, D is D20. In some embodiments, D is D21. In someembodiments, D is D22. In some embodiments, D is D23. In someembodiments, D is D24. In some embodiments, D is D25. In someembodiments, D is D26. In some embodiments, D is D27. In someembodiments, D is D28. In some embodiments, D is D29. In someembodiments, D is D30. In some embodiments, D is D31. In someembodiments, D is D32. In some embodiments, D is D33. In someembodiments, D is D34. In some embodiments, D is D35. In someembodiments, D is D36. In some embodiments, D is D37.

In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7.In some embodiments, D is selected from D8, D9, D10, D11, D12, D13, andD14. In some embodiments, D is selected from D15, D16, D17, D18, D19,D20, and D21. In some embodiments, D is selected from D22, D23, D24,D25, D26, D27, and D28. In some embodiments, D is selected from D29,D30, D31, D32, D33, D34, and D35. In some embodiments, D is selectedfrom D36, D37.

In some embodiments, two instances of D are the same. In someembodiments, all instances of D are the same.

In some embodiments, Z is H. In some embodiments, Z is Me. In someembodiments, Z is t-Bu. In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

in some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments, Z is

In some embodiments the compound of Formula (II) is selected from:

5,5′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(5H-benzo[b]carbazole);

4-(3-phenyl-2,5,6-tris(5H-pyrido[4,3-b]indol-5-yl)pyridin-4-yl)benzonitrile;

5-(4-(4-(6-methylpyridin-2-yl)phenyl)-3,5-diphenylpyridin-2-yl)-10-phenyl-5,10-dihydrophenazine;

9′-(4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9′,9″″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

9,9′-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(3-(3,6-diphenyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)benzonitrile;

9,9′-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(3,5-bis(5H-pyrido[4,3-b]indol-5-yl)pyridin-4-yl)benzonitrile;

4-(2 -(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile;

9-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)-3,6-diphenyl-9H-carbazole;

7,7′,7″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

9′-(5-phenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

9′,9″″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(9′H-9,3′:6′,9′-tercarbazole);

9,9′,9″-(4-(4-(pyridin-3-yl)phenyl)-pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole);

9′,9″″-(4-(4-(6-methylpyridin-2-yl)phenyl)-2,6-diphenylpyridine-3,5-diyl)bis((9′H-9,2′:7′,9″-tercarbazole));

4-(2,3,5,6-tetrakis(7H-benzo[c]carbazol-7-yl)pyridin-4-yl)benzonitrile;

9′-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9-(4-(4-(6-methylpyridin-2-yl)phenyl)-5-phenylpyridin-3-yl)-N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine;

5-(4-(4-(2,6-dimethylpyridin-3-yl)phenyl)pyridin-2-yl)-10-phenyl-5,10-dihydrophenazine;

9′-(5-phenyl-4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

7,7′,7″-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl-5-phenylpyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

9′,9″″-(3,5-diphenyl-4-(4-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

N2,N2,N7,N7-tetraphenyl-9-(4-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridin-3-yl)phenyl)-9H-carbazole-2,7-diamine;

9,9′,9″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(9H-pyrido[3,4-b]indole);

9′-(3,5,6-triphenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole

7,7′,7″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(7H-benzo[c]carbazole);

9,9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

9,9-diphenyl-10-(2-phenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-3-yl)-9,10-dihydroacridine;

10,10′,10″-(6-phenyl-4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(9,9-diphenyl-9,10-dihydroacridine);

9′,9″″-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

9-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2-phenylpyridin-3-yl)phenyl)-3,6-diphenyl-9H-carbazole;

7,7′,7″-(4-(4-(2,6-diphenylpyrimidin-4-y)phenyl)-6-phenylpyridine-2,3,5-triyl)tris(7H-benzo[c]carbazole);

4-(2-(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)-3,5-diphenylpyridin-4-yl)benzonitrile;

7,7′-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(7H-benzo[c]carbazole);

9,9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

9,9′,9″-(4-(4-(6-methylpyridin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole);

9,9′-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

9′,9″″-(4-(4-(pyridin-3-yl)phenyl)pyridine-2,3-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

9,9′,9″,9′″-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-4,5-dicarbonitrile);

5,5′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(5H-benzo[b]carbazole);

9,9′-((4(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-3,5-diyl)bis(4,1-phenylene))bis(3,6-diphenyl-9H-carbazole);

9,9′-(4-(4-(pyridin-3-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

9,9′,9″-(6-phenyl-4-(4-(pyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole);

9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5-diphenylpyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′-(4-(4-(pyridin-4-yl)phenyl)pyridin-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-3-yl)-3,6-diphenyl-9H-carbazole;

5-(4-(4-(2,6-dimethylpyridin-3-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)-10-phenyl-5,10-dihydrophenazine;

9,9′-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

9′,9″″-(5,6-diphenyl-4-(4-(pyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

9′-(4-(4-(4-(4,6-diphenyl-1,3,5-thazin-2-yl)phenyl)pyridin-3-yl)phenyl)-9′H-9,3′:6′,9″-tercarbazole;

9′-(4-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-3-phenylpyridin-2-yl)phenyl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′-(4-(4-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(3,5-bis(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile;

4-(3-(4-(9′H-[9,3′:6′,9″-tercarbazol]yl)phenyl)-5-phenylpyridin-4-yl)benzonitrites;

4-(2,3,6-tris(2,7-diphenyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)benzonitrile;

5,5′,5″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenylpyridine-2,3,5-triyl)tris(5H-benzo[b]carbazole);

9′-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2-phenylpyridin-3-yl)phenyl)-9′H-9,3′:6′,9″-tercarbazole;

9′-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)phenyl)-9′H-9,2′:7′,9″-tercarbazole;

9,9′-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)-5,6-diphenylpyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

9,9′-((4(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3,6-diphenyl-9H-carbazole);

9′-(4-(4-(pyridin-3-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

4-(2,3,5-tris(9,9-diphenylacridin-10(9H)-yl)-6-phenylpyridin-4-yl)benzonitrile,

9,9′,9″-(5-phenyl-4-(4-(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole);

9,9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5-diphenylpyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

9,9′-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

7,7′,7″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

5-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin)-10-phenyl-5,10-dihydrophenazine;

11,11′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(11H-benzo[a]carbazole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-3-yl)-1,8-diphenyl-9H-carbazole;

9-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3phenylpyridin-2-yl)-9H-pyrido[3,4-b]indole;

10-(3,5,6-triphenyl-4-(4-(pyridin-3-yl)phenyl)pyridin-2-yl-10H-phenoxazine;

4-(2-(2,7-diphenyl-9H-carbazol-9-yl)-3-phenylpyridin-4-yl)benzonitrile;

10,10′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(9,9-diphenyl-9,10-dihydroacridine);

9′-(4-(4-(2,6-diphenylpyridin-4yl)phenyl)pyridin-2-yl)9′H-9,3′:6′,9″-tercarbazole;

9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′-(4-(4-cyanophenyl)pyridine-2,6-diyl)bis(9H-carbazole-3,6-dicarbonitrite);

4-(2,3,5-tris(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile;

7,7′-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(7H-benzo[c]carbazole);

10-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyridin-3-yl)-9,9-diphenyl-9,10-dihydroacridine;

7,7′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(7H-benzo[c]carbazole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-3-phenylpyridin-2-yl)-3,6-diphenyl-9H-carbazole;

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyridin-3-yl)-3,6-diphenyl-9H-carbazole;

5-phenyl-10-(2-phenyl-4-(4-(pyridin-3-yl)phenyl)pyridin-3-yl)-5,10-dihydrophenazine;

9,9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2,6-diphenylpyridine-3,5-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(2-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)-3,5,6-triphenylpyridin-4-yl)benzonitrile;

9′-(4-(4-(pyridin-3-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′,9″-(5-phenyl-4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole);

9,9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2,6-diphenylpyridine-3,5-diyl)bis(3,6-diphenyl-9H-carbazole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-5-phenylpyridin-3-yl)-3,6-diphenyl-9H-carbazole;

3,6-diphenyl-9-(2-phenyl-4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridin-3-yl)-9H-carbazole;

9,9′-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

7,7′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(7H-benzo[c]carbazole):

9′-(4-(4-(2,6-diphenylpyridin-3-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

4-(2,3,6-tris(9,9-diphenylacridin-10(9H)-yl)-5-phenylpyridin-4-yl)benzonitrile;

9′,9″″-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

4-(2-(2,7-bis(diphenylamino)-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)benzonitrile;

10-(5-phenyl-4-(4-(pyridin-4-yl)phenyl)pyridin-3-yl)-10H-phenoxazine;

4(3-phenyl-2,5,6-tris(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)benzonitrile;

7,7′,7″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

10,10′-(2,6-diphenyl-4-(4-(pyridin-2-yl)phenyl)pyridine-3,5-diyl)bis(5-phenyl-5,10-dihydrophenazine);

5-phenyl-10-(2,5,6-triphenyl-4-(4-(pyridin-3-yl)phenyl)pyridin-3-yl)-5,10-dihydrophenazine;

9′-(2-phenyl-4-(4-(pyridin-3-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

5,5′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-3,5-diyl)bis(5H-pyrido[3,2-b]indole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2,5,6-triphenylpyridin-3-yl)-3,6-diphenyl-9H-carbazole;

10,10′,10″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-phenylpyridine-2,3,5-triyl)tris(10H-phenoxazine);

9(4-(4-(2,6-diphenylpyrimidin-4-y)phenyl)-3,5,6-triphenylpyridin-2-yl)-3,6diphenyl-9H-carbazole;

4-(2,3,5,6-tetrakis(5H-pyrido[3,2-b]indol-5-yl)pyridin-4-yl)benzonitrile;

7,7′,7″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-y)phenyl)-6-phenylpyridine-2,3,5-triyl)tris(7H-benzo[c]carbazole);

3,6-diphenyl-9-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridin-2-yl)-9H-carbazole;

10,10′-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,6-diyl)bis(9,9-diphenyl-9,10-dihydroacridine);

9-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)-3,6-diphenyl-9H-carbazole;

9′,9″″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

4-(2,6-bis(9,9-diphenylacridin-10(9H)-yl)pyridin-4-yl)benzonitrile;

4-(2,3,6-tris(11H-benzo[a]carbazol-11-yl)-5-phenylpyridin-4-yl)benzonitrile;

9′,9″″-(4-(4-(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

9,9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

5-phenyl-10-(4-(4-(pyridin-3-yl)phenyl)pyridin-2-yl)-5,10-dihydrophenazine;

10,10′-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-3,5-diyl)bis(5-phenyl-5,10-dihydrophenazine);

9,9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-3,5-diyl)bis(3,6-diphenyl-9H-carbazole);

10-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-3-yl)-10H-phenoxazine:

4-(2,6-bis(7H-benzo[c]carbazol-7-yl)pyridin-4-yl)benzonitrile;

7,7′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-5,6-diphenylpyridine-2,3-diyl)bis(7H-benzo[c]carbazole);

9,9′-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole);

9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-2-yl-9′H-9,3′:6′,9″-tercarbazole;

9,9′,9″-(4-(4-(pyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbzole);

4-(2,3-bis(3,6-diphenyl-9H-carbazol-9-yl)-5,6-diphenylpyridin-4-yl)benzonitrile;

4-(2,3-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile;

9′-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2,5,6-triphenylpyridin-3-yl)phenyl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′-(5,6-diphenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);7,7′,7″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

10,10′-(4-(4-(pyridin-2-yl)phenyl)pyridine-3,5-diyl)bis(5-phenyl-5,10-dihydrophenazine);

10-(4-(4-(6-methylpyridin-2-yl)phenyl)pyridin-3-yl)-10H-phenoxazine;

4-(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile;

9′-(4-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2,5,6-triphenylpyridin-3-yl)phenyl)-9′H-9,2′:7′,9″-tercarbazole;

7,7′,7″,7′″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(7H-benzo[c]carbazole);

4-(2,3,5,6-tetrakis(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)benzonitrile;

4-(2-(10-phenylphenazin-5(10H)-yl)pyridin-4-yl)benzonitrile;

9,9′-((4(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3,6-diphenyl-9H-carbazole);

9′,9″″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

4-(2,6-bis(11H-benzo[a]carbazol-11-yl)pyridin-4-yl)benzonitrile;

4-(3,5-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile;

4-(3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile;

4-(3-(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile;

4-(3-(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)-2-phenylpyridin-4-yl)benzonitrile;

4-(2-(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)-3-phenylpyridin-4-yl)benzonitrile;

9′,9″″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

11,11′,11″,11′″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(11H-benzo[a]carbazole);

N3,N3,N6,N6-tetraphenyl-9-(4-(4-(pyridin-4-yl)phenyl)pyridin-3-yl)-9H-carbazole-3,6-diamine;

10-(4-(4-(2,6-diphenylpyridin-3-yl)phenyl)-2-phenylpyridin-3-yl)-10H-phenoxazine;

9-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridin-3-yl)phenyl)-3,6-diphenyl-9H-carbazole;

10,10′-(4-(4-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(9-diphenyl-9,10-dihydroacridine);

4-92,6-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)-3,5-diphenylpyridin-4-yl)benzonitrile;

7,7′,7″-(5-phenyl-4-(4-(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

4-(3-(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile;

9′-(4(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-3,5-diphenylpyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9′-(3,5-diphenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′,9″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole);

4-(2,3-bis(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile;

9,9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-3,5-diyl)bis(3,6-diphenyl-9H-carbazole);

10-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)-9,9-diphenyl-9,10-dihydroacridine;

9′-phenyl-9′H-9,2′;7′,9″-tercarbazole;

4-(2,3,5-tris(3,6-diphenyl-9H-carbazol-9-yl)-6-phenylpyridin-4-yl)benzonitrile;

9,9′,9″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole):

7,7′,7″-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(7H-benzo[c]carbazole);

4-(3-(9,9-dimethylacridin-10(9H)-yl-2-phenylpyridin-4-yl)benzonitrile;

7,7′,7″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(7H-benzo[c]carbazole);

10-(2,5,6-triphenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-3-yl-10H-phenoxazine;

5-phenyl-10-(4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-5,10-dihydrophenazine;

10,10′-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(9,9-diphenyl-9,10-dihydroacridine);

9′-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)-2-phenylpyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole;

9,9′,9″-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole);

4-(2,3,5-tri(10H-phenoxazin-10-yl)pyridin-4-yl)-benzonitrile;

9,9′,9″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole);

9-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridin-3-yl)-3,6-diphenyl-9H-carbazole;

9′-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3-phenylpyridin-2-Y)phenyl)-9′H-9,3′:6′,9″-tercarbazole:

9,9′-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

5,5′,5″-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,3,5-triyl)tris(5H-benzo[b]carbazole);

9,9′,9″-(5-phenyl-4-(4-(pyridin-3-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole);

9′,9″″-(5,6-diphenyl-4-(4-(pyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

N3,N3,N6,N6-tetraphenyl-9-(4-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridin-3-yl)phenyl)-9H-carbazole-3,6-diamine;

4-(2,6-bis(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile;

5,5′,5″,5′″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-benzo[b]carbazole);

9,9′-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)-5,6-diphenylpyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(3-phenyl-2,5,6-tris(5H-pyrido[3,2-b]indol-5-yl)pyridin-4-yl)benzonitrile;

9,9′,9″,9′″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole);

4-(3-(3,6-diphenyl-9H-carbazol-9-yl)-2-phenylpyridin-4-yl)benzonitrile;

9′-(4-(4-(6-methylpyridin-2-yl)phenyl)-5-phenylpyridin-3-yl)-(9′H-9,3′:6′,9″-tercarbazole;

9-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl-3-phenylpyridin-2-yl)phenyl)-3,6-diphenyl-9H-carbazole;

4-(2,3,6-tris(7H-benzo[c]carbazol-7-yl)-5-phenylpyridin-4-yl)benzonitrile;

10-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridin-3-yl)-9,9-diphenyl-9,10-dihydroacridine;

9-(4-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3yl)-phenyl)-3,6-diphenyl-9H-carbazole;

9′,9″″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

9-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-2-yl)-3,6-diphenyl-9H-carbazole;

9′,9″″-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));

10,10′-(4-(4-(pyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(10H-phenoxazine);

10,10′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(9,9-diphenyl-9,10-dihydroacridine);

9,9′,9″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole);

5-phenyl-10-(2,5,6-triphenyl-4-(4-(pyridin-4-yl)phenyl)pyridin-3-yl)-5,10-dihydrophenazine;

9-(4-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)phenyl)-N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine;

4-(2-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)-3,5-diplienylpyridin-4-yl)benzonitrile;

4-(2-(3,6-diphenyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)benzonitrile;9′-(4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,2′:7′,9″-tercarbazole;

4-(2-(4-(2,7-bis(diphenylamino)-9H-carbazol-9-yl)phenyl-3,5-diphenylpyridin-4-yl)benzonitrile;

5-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-3-yl)-5H-benzo[b]carbazole;

9′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)-9′H-9,2′:7′,9″-tercarbazole;

9′,9″-(4-(4-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-3,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole);

9-(4-(4-(6-methylpyridin-2-yl)phenyl)-2-phenylpyridin-3-yl)-N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine;

10,10′,10″-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(9,9-diphenyl-9,10-dihydroacridine);

11,11′-(4-(4-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(11H-benzo[a]carbazole);

4-(3-(9′H-[9,3′:6′,9″-tercarbazal]-9′-yl)-2-phenylpyridin-4-yl)benzonitrile;

10-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)-5-phenylpyridin-3-yl)-10H-phenoxazine;9,9′-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole);

4-(2,3,6-tris(4,5-diphenyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)benzonitrile;

9′-(3-phenyl-4-(4-(pyridin-2-yl)phenyl)pyridin-2-yl)-9′H-9,3′:6′,9″-tercarbazole;

5-phenyl-10-(4-(4-(6-phenylpyridin-2-yl)phenyl)pyridin-2-yl)-5,10-dihydrophenazine;

9-(4-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridin-2-yl)-3,6-diphenyl-9H-carbazole;

9-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2-phenylpyridin-3-yl)-3,6-diphenyl-9H-carbazole;

7,7′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5,6-diphenylpyridine-2,3-diyl)bis(7H-benzo[c]carbazole);and

7,7′,7″,7′″-(4-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(7H-benzo[c]carbazole).

In some embodiments the compound of Formula (II) is selected from

In some embodiments, the compounds have a structure of Formula (III):

wherein

A is selected from CN,

D is independently selected from H, Ph,

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one instance of D is selected from D1-D31.

In some embodiments, A is CN. In some embodiments, A is A1. In someembodiments, A is A2. In some embodiments, A is A3. In some embodiments,A is A4. In some embodiments, A is A5. In some embodiments, A is A6. Insome embodiments, A is A7.

In some embodiments, A is selected from A1, A2, and A3. In someembodiments, A is selected from A4 and A5. In some embodiments, A isselected from A6 and A7.

In some embodiments, D is H. In some embodiments, at least one instanceof D is H. In some embodiments, D is Me. In some embodiments, at leastone instance of D is Me. In some embodiments, D is Ph. In someembodiments, at least one instance of D is Ph.

In some embodiments, D is D1. In some embodiments, D is D2. In someembodiments, D is D3. In some embodiments, D is D4. In some embodiments,D is D5. In some embodiments, D is D6. In some embodiments, D is D7. Insome embodiments, D is D8. In some embodiments, D is D9. In someembodiments, D is D10. In some embodiments, D is D11. In someembodiments, D is D12. In some embodiments, D is D13. In someembodiments, D is D14. In some embodiments, D is D15. In someembodiments, D is D16. In some embodiments, D is D17. In someembodiments, D is D18. In some embodiments, D is D19. In someembodiments, D is D20. In some embodiments, D is D21. In someembodiments, D is D22. In some embodiments, D is D23. In someembodiments, D is D24. In some embodiments, D is D25. In someembodiments, D is D26. In some embodiments, D is D27, In someembodiments, D is D28. In some embodiments, D is D29. In someembodiments, D is D30. In some embodiments, D is D31.

In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7.In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13.In some embodiments, D is selected from D14, D15, and D16. In someembodiments, D is selected from D17, D18, and D19. In some embodiments,D is selected from D20, D21, D22, D23, and D24. In some embodiments, Dis selected from D25, D26, and D27. In some embodiments, D is selectedfrom D28, D29, D30, and D31.

In some embodiments, R is H. In some embodiments, R is Me. In someembodiments, R is Ph.

In some embodiments, both instances of R are different. In someembodiments, both instances of R are the same.

In some embodiments, each instance of D is different. In someembodiments, two instances of D are the same. In some embodiments, threeinstances of D are the same. In some embodiments, all instances of D arethe same.

In some embodiments, two instances of D are independently selected fromD1-D31. In some embodiments, three instances of D are independentlyselected from D1-D31. In some embodiments, all instances of D areindependently selected from D1-D31.

In some embodiments, Z₁ is C(CH₃)₂. In some embodiments, Z₁ is C(Ph)₂.In some embodiments, Z₁ is O. In some embodiments, Z₁ is C(CH₃)₂. Insome embodiments, Z₁ is N(Ph).

In some embodiments, Z₂ is H. In some embodiments, Z₂ is CN. In someembodiments, Z₂ is (C₁-C₂₀)-alkyl. In some embodiments, Z₂ is5-30-membered aryl. In some embodiments, Z₂ is 3-30-membered heteroaryl.In some embodiments, Z₂ is diarylamino. In some embodiments, diarylaminois —N(Ph)₂.

In some embodiments, the two instances of Z₂ are the same. In someembodiments, the two instances of Z₂ are different.

In some embodiments the compound of Formula (III) is selected from

5,5′,5″,5′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

3-(2,3,5,6-tetra(9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

9,9′,9″,9′″-(4-(3-(2,6-diphenylpyridin-4-yl)phenyl)pyridin-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(N3,,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,5-diyl)bis((9′H-9,3′:6′,9″-tercarbazole))

9,9′-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis((9H-9,3′:6′,9″-tercarbazole))

5,5′,5″,5′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

9,9′,9″,9′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(2,7-dimethyl-9H-carbazole)

9,940,9″,9′″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(4,5-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′-(4-(3-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4-yl)phenyl)pyridine-2,5-diyl)bis(3,6-diphenyl-9H-carbazole)

9,9′-((4-(3-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene)bis(4,5-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(4,5-diphenyl-9H-carbazole)

9,9′-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(9H-carbazole)

9′,9″″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9,9′-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole)

9,9′-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(4,5-dimenthyl-9H-carbazole)

9,9′-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis((9′H-9,3′:6′,9″-tercarbazole))

9,9′,9″-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9′,9″″-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9,9′-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole))

9,9′-((4-(3-(pyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-((4-(3-(pyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(4,5-diphenyl-9H-carbazole)

9,9′-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9,9′,9″,9′″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(4,5-dimethyl-9H-carbazole)

4,4′-(4-(3-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(9-phenyl-9H-carbazole)

3-(2,3,6-tris(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(2-(9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(4-(4,5-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(4-(9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,6-tri(9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,6-tris(4,5-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

9,9′-(4-(3-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-dimethyl-9H-carbazole)

9,9′-(4-(3-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9,9′-(4-(3-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole)

9,9′-((4-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(2,7-diphenyl-9H-carbazole)

9,9′-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9′,9″″-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,4′:5′,9″-tercarbazole)

9,9′-(4-(3-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(9′H-9,4′:5′,9″-tercarbazole)

9,9′,9″,9′″-(4-(3-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′-(4-(3-(pyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9,9′-(4-(3-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9,9′-(4-(3-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-1-carbazole-3,6-diamine)

9′,9″″-(4-(3-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9,9′,9″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′-((4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(9H-carbazole-2,7-dicarbonitrile)

9,9′(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole)

3-(2,6-bis(4-(3,6-bis(diphenylamino)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,6-bis(2-(3,6-bis(diphenylamino)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,6-bis(4-(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,6-bis(3,6-bis(diphenylamino)-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,6-di(9′H-[9,3′:6,′9″-tercarbazol]-yl)pyridin-4-yl)benzonitrile

3(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,6-bis(4,5-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

9,9′,9″,9′″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(4,5-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

3-(2,3,5-tris(5H-pyrido[4,3-b]indol-5-yl)pyridin-4-yl)benzonitrile

3-(2,3,5-tris(4-(4,5-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,3,5-tri(9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5-tris(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5-tris(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5-tris(4-(4,5-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

5,5′,5″-5′″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

9,9′-((4-(3-(pyridin-3-yl)phenyl)pyridine-3,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-(4-(3-(pyridin-3-yl)phenyl)pyridine-3,5-diyl)bis(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-pyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(pyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

9′,9″″-(4-(3-(2,6-dimenthylpyridin-4-yl)phenyl)pyridine-3,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

3-(2,5-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(2,5-bis(4-(9′H-[9,3′:6′.9″-tercarbazol]-9′-y)phenyl)pyridin-4-yl)benzonitrile

3-(2,5-bis(4,5-bis(diphenylamino)-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,5-bis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,5-di(9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,5-bis(4-(9′H-[9,4′:5′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile

9,9′,9″-(4-(3-(pyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(4,5-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(4,5-diphenyl-9H-carbazole)

9,9′-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-3,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9,9′-(4(4-(3-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(4,5-diphenyl-9H-carbazole)

9,9′-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole))

9′,9″″-((4-(3-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis((9′H-9,4′:5′,9″-tercarbazole))

9′,9″″-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(4,5-dimethyl-9H-carbazole)

9,9′-(4-(3-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(N4,N4,N5,N5-tetraphenyl-9H-carbazole-4,5-diamine)

9,9′-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis((9′H-9,3′:6′,9″-tercarbazole))

9,9′-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole)

3-(3,5-bis(4-(3,6-bis(diphenylamino)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)benzonitrile

3-(3,5-bis(4-9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)phenyl)pyridin-4-yl)benzonitrile

3-(3,5-bis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5,6-tetrakis(3H-pyrido[4,3-b]indol-5-yl)pyridin-4-yl)benzonitrile

3-(2,3,5,6-tetrakis(5H-pyrido[3,2-b]indol-5-yl)pyridin-4-yl)benzonitrile

3-(2,3,5,6-tetrakis(1,8-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5,6-tetrakis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

3-(2,3,5,6-tetrakis(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)benzonitrile

9,9′,9″,9′″-(4-(3-cyanophenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-4,5-dicarbonitrile)

3-(2,3,5,6-tetrakis(4,5-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)benzonitrile

9,9′,9″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

5,5′,5″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(5H-pyrido[3,2-b]indole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-pyrido[3,4-b]indole)

9,9′,9″-(4-(3-(4,6-diphenyl-1,3,5triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(4,5-diphenyl-9H-carbazole)

9,9′,9″-(4-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole)9,9′-(4-(3-(pyridin-4-yl)phenyl)pyridine-3,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9,9′,9″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-carbazole)

9,9′,9″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

9,9′-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(N3,N3,N6,N6-tetraphenyl-9H-carbazole-3,6-diamine)

9′,9″″-(4-(3-(6-phenylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis((9′H-9,3′:6′,9″-tercarbazole));and

9,9′,9″-(4-(3-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-diphenyl-9H-carbazole)

In some embodiments, the compound of Formula (III) is selected from

In some embodiments, the compound of formula (III) is

In some embodiments, the compounds have a structure of Formula (IV):

wherein

A is selected from CN,

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂, C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one instance of D is selected from D1-D31.

In some embodiments, A is CN. In some embodiments, A is A1. In someembodiments, A is A2. In some embodiments, A is A3. In some embodiments,A is A4. In some embodiments, A is A5. In some embodiments, A is A6. Insome embodiments, A is A7.

In some embodiments, A is selected from A1, A2, and A3. In someembodiments, A is selected from A4 and A5. In some embodiments, A isselected from A6 and A7.

In some embodiments, D is D 1. In some embodiments, D is D2. In someembodiments, D is D3. In some embodiments, D is D4. In some embodiments,D is D5. In some embodiments, D is D6. In some embodiments, D is D7. Insome embodiments, D is D8. In some embodiments, D is D9. In someembodiments, D is D10. In some embodiments, D is D11. In someembodiments, D is D12. In some embodiments, D is D13. In someembodiments, D is D14. In some embodiments, D is D15. In someembodiments, D is D16. In some embodiments, D is D17. In someembodiments, D is D18. In some embodiments, D is D19. In someembodiments, D is D20. In some embodiments, D is D21. In someembodiments, D is D22. In some embodiments, D is D23. In someembodiments, D is D24. In some embodiments, D is D25. In someembodiments, D is D26. In some embodiments, D is D27. In someembodiments, D is D28. In some embodiments, D is D29. In someembodiments, D is D30. In some embodiments, D is D31.

In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7.In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13.In some embodiments, D is selected from D14, D15, and D16. In someembodiments, D is selected from D17, D18, and D19. In some embodiments,D is selected from D20, D21, D22, D23, and D24. In some embodiments, Dis selected from D25, D26, and D27. In some embodiments, D is selectedfrom D28, D29, D30, and D31.

In some embodiments, R is H. In some embodiments, R is Me. In someembodiments, R is Ph.

In some embodiments, both instances of R are different. In someembodiments, both instances of R are the same.

In some embodiments, each instance of D is different. In someembodiments, two instances of D are the same. In some embodiments, threeinstances of D are the same. In some embodiments, all instances of D arethe same.

In some embodiments, two instances of D are independently selected fromD1-D31. In some embodiments, three instances of D are independentlyselected from D1-D31. In some embodiments, all instances of D areindependently selected from D1-D31.

In some embodiments, Z₁ is C(CH₃)₂. In some embodiments, Z₁ is C(Ph)₂.In some embodiments. Z₁ is O. In some embodiments, Z₁ is C(CH₃)₂. Insome embodiments, Z₁ is N(Ph).

In some embodiments, Z₂ is H. In some embodiments, Z₂ is CN. In someembodiments, Z₂ is (C₁-C₂₀)-alkyl. In some embodiments, Z₂ is5-30-membered aryl.

In some embodiments, Z₂ is 3-30-membered heteroaryl. In someembodiments, Z₂ is diarylamino. In some embodiments, diarylamino is—N(Ph)₂.

In some embodiments, the two instances of Z₂ are the same. In someembodiments, the two instances of Z₂ are different.

In some embodiments the compound of Formula (IV) is selected from

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)-tetrakis(3-phenyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-phenyl-9H-carbazole)

2-(2-(2,3,5,6-tetrakis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phenyl)benzo[d]oxazole

9,9′,9″,9′″-(4-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

2-(2-(2,3,5,6-tetrakis(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)phenyl)benzo[d]thiazole

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(benzo[d]oxazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

5,5′,5″,5′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

11,11′,11″,11′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(11H-benzo[a]carbazole)

5,5′,5″,5′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-((4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(benzene-4,1-diyl))tetrakis(3-methyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-(4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

5,5′,5″,5′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-benzo[b]carbazole)

5,5′,5″,5′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

5,5′,5″,5′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

5,5′,5″,5′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

5,5′,5″,5′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-benzo[b]carbazole)

7,7′,7″,7′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(7H-benzo[c]carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(pyridine-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-phenyl-9H-carbazole)

9,9′,9″,9′″-(4-(2(1-phenyl-1H-benzo[d]imidazol-2-phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

1,1′,1″,1′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9-phenyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridin-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-((4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(benzene-4,1-diyl))tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H--carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

11,11′,11″,11′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(11H-benzo[a]carbazole)

9,9′,9″,9′″-(4(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

2-(2-(2,3,5,6-tetra(9H-carbazol-9-yl)pyridin-4-yl)phenyl)benzo[d]oxazole

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-((4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(benzene-4,1-diyl))tetrakis(3-methyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

9,9′,9″,9′″-(4-(2-(benzo[d]thiazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

5,5′,5″,5′″-(4-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[1,3-b]indole)9,9′,9″,9′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

9,9′,9″,9′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

2-(2-(2,3,5,6-tetrakis(5H-pyrido[3,2-b]indol-5-yl)pyridin-4-yl)phenyl)benzo[d]oxazole

2-(2-(2,3,5,6-tetrakis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phenyl)benzo[d]thiazole

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-pyrido[3,4-b]indole)

4,4′,4″,4′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9-phenyl-9H-carbazole)

9,9′,9″,9′″-((4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(benzene-3,1-diyl))tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-(4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridin-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridone-2,3,5,6-tetrayl)tetrakis(3-phenyl-9H-carbazole)

5,5′,5″,5′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[3,2-b]indole)

9,9′,9″,9′″-(4-(2-(pyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

2-(2-(2,3,5,6-tetra(9H-carbazol-9-yl)pyridin-4-yl)phenyl)benzo[d]thiazole

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,35,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″,9′″-(4-(2-(pyridin-2-yl)phenyl)pyridin-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

9,9′,9″,9′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole)

9,9′,9″,9′″-((4-(2-(pyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(benzene-4,1-diyl))tetrakis(9H-carbazole-3-carbonitrile)

9,9′,9″,9′″-(4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-methyl-9H-carbazole)

10,10′,10″,10′″-(4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(10H-phenoxazine)

9,9′,9″,9′″-(4-(2-(pyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

9,9′,9″,9′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3-(tert-butyl)-9H-carbazole)

5,5′,5″,5′″-(4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

5,5′,5″,5′″-(4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(5H-pyrido[4,3-b]indole)

9,9′,9″,9′″-(4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole);and

9,9′,9″,9′″-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,5,6-tetrayl)tetrakis(3,6-dimethyl-9H-carbazole)

In some embodiments, the compound of Formula (IV) is selected from

In some embodiments, the compounds have a structure of Formula (V):

wherein

A is selected from CN,

D₁ and D₄ are independently selected from Ph and D;

D₂ and D₃ are independently selected from H, deuterium, Ph, and D;

D is independently selected from

R is independently selected from H, Me, and Ph;

Z₁ is independently selected from C(CH₃)₂. C(Ph)₂, O, and N(Ph);

Z₂ is independently selected from H, CN, (C₁-C₂₀)-alkyl, 5-30-memberedaryl, 3-30-membered heteroaryl, and diarylamino; and

at least one D1, D2, D3, and D4 is D.

In some embodiments, A is CN. In some embodiments, A is A1. In someembodiments, A is A2. In some embodiments, A is A3. In some embodiments,A is A4. In some embodiments, A is A5. In some embodiments, A is A6. Insome embodiments, A is A7.

In some embodiments, A is selected from A1, A2, and A3, In someembodiments, A is selected from A4 and A5. In some embodiments, A isselected from A6 and A7.

In some embodiments, D₁ is Ph. In some embodiments, D₁ is D.

In some embodiments, D₂ is H. In some embodiments, D₂ is deuterium. Insome embodiments, D₂ is Ph. In some embodiments, D₂ is D.

In some embodiments, D₃ is H. In some embodiments, D₃ is deuterium. Insome embodiments, D₃ is Ph. In some embodiments, D₃ is D.

In some embodiments, D₄ is Ph. In some embodiments, D₄ is D.

In some embodiments, D is D1. In some embodiments, D is D2. In someembodiments, D is D3. In some embodiments, D is D4. In some embodiments,D is D5. In some embodiments, D is D6. In some embodiments, D is D7. Insome embodiments, D is D8. In some embodiments, D is D9. In someembodiments, D is D10. In some embodiments, D is D11. In someembodiments, D is D12. In some embodiments, D is D13. In someembodiments, D is D14. In some embodiments, D is D15. In someembodiments, D is D16. In some embodiments, D is D17. In someembodiments, D is D18. In some embodiments, D is D19. In someembodiments, D is D20. In some embodiments, D is D21. In someembodiments, D is D22. In some embodiments, D is D23. In someembodiments, D is D24. in some embodiments, D is D25. In someembodiments, D is D26. In some embodiments, D is D27. In someembodiments, D is D28. In some embodiments, D is D29. In someembodiments, D is D30. In some embodiments, D is D31.

In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7.In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13.In some embodiments, D is selected from D14, D15, and D16. In someembodiments, D is selected from D17, D18, and D19. In some embodiments,D is selected from D20, D21, D22, D23, and D24. In some embodiments, Dis selected from D25, D26, and D27. In some embodiments, D is selectedfrom D28, D29, D30, and D31.

In some embodiments, R is H. In some embodiments, R is Me. In someembodiments, R is Ph.

In some embodiments, both instances of R are different. In someembodiments, both instances of R are the same.

In some embodiments, each instance of D is different. In someembodiments, two instances of D are the same. In some embodiments, threeinstances of D are the same. In some embodiments, all instances of D arethe same.

In some embodiments, two instances of D are independently selected fromD1-D31. In some embodiments, three instances of D are independentlyselected from D1-D31. In some embodiments, all instances of D areindependently selected from D1-D31.

In some embodiments, Z₁ is C(CH₃)₂. In some embodiments, Z₁ is C(Ph)₂.In some embodiments, Z₁ is 0. In some embodiments, Z₁ is C(CH₃)₂. Insome embodiments, Z₁ is N(Ph).

In some embodiments, Z₂ is H. In some embodiments, Z₂ is CN. In someembodiments, Z₂ is (C₁-C₂₀)-alkyl. In some embodiments, Z₂ is methyl,isopropyl and tert-butyl. In some embodiments, Z₂ is 5-30-membered aryl.In some embodiments, Z₂ is 3-30-membered heteroaryl. In someembodiments, Z₂ is diarylamino. In some embodiments, diarylamino is—N(Ph)₂.

In some embodiments, the two instances of Z₂ are the same. In someembodiments, the two instances of Z₂ are different.

In some embodiments the compound of Formula (V) is selected from

9,9′-((3,5-bis(dibenzo[b,d]furan-1-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene)bis(3-methyl-9H-carbazole)

9,9′-((6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(2,1-phenylene))bis(9H-carbazole-3-carbonitrile)

5,5′-(6-(4-(3,6-bis(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[3,2-b]indole)

9,9″-(6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3-diyl)bis((9H-3,9′-bicarbazole))

9,9′-((9-(4-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)-3,5,6-triphenylpyridin-2-yl)phenyl)-9H-carbazole-3,6-diyl)bis(4,1-phenylene))bis(9H-carbazole)

9,9′-(6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-((3-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene)bis(9H-carbazole)

5,5′-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

5,5′-(3,6-bis(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[3,2-b]indole)

9,9′-((3-(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(3,1-phenylene))bis(9H-carbazole-3-carbonitrile)

9,9′-((6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

5-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2,6-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-3-yl)-5H-pyrido[4,3-b]indole

9′-(2,5,6-tris(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridin-3-yl)-9′H-9,3′:6′,9″-tercarbazole

9,9′-(3-(3-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridin-2,6-diyl)bis(3,6-di-tert-butyl-9H-carbazole)

9,9′-((6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(9H-carbazole)

9-(3,6-bis(3,6-diphenyl-9H-carbazol-9-yl)-4-(2-(pyridin-2-yl)phenyl)pyridin-2-yl)-9H-carbazole-3-carbonitrile

11,11′,11″-(5-(3-(tert-butyl)-9H-carbazol-9-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(11H-benzo[a]carbazole)

9,9′,9″-(6-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-2,3,5-triyl)tris(3-methyl-9H-carbazole)

9,9′-(6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(3,6-diphenyl-9H-carbazole)

9-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)-2,6-bis(5H-pyrido[4,3-b]indol-5-yl)pyridin-3-yl)-9H-carbazole-3-carbonitrile

5-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5,6-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-2-yl)-5H-pyrido[4,3-b]indole

5,5′-(6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(5H-pyrido[3,2-b]indole)

9,9′-((4-(2-(6-methylpyridin-2-yl)phenyl)-2,6-bis(9-phenyl-9H-carbazol-2-yl)pyridine-3,5-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9-(4-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-2-yl)phenyl)-9H-carbazole-3-carbonitrile

9,9′-((3-(4-(3-cyano-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenylpyrimidin-2yl)phenyl)pyridine-2,6-diyl)bis(3,1-phenylene))bis(9H-carbazole-3,6-dicarbonitrile)

10-(2,5,6-tris(4-(3-methyl-9H-carbazol-9-yl)phenyl)-4-(2-(6-phenylpyridin-2-yl)phenyl)pyridin-3-yl)-10H-phenoxazine

9,9′-(3-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazole)

N,N-diphenyl-4-(9-(4-(3,5,6-tris(3-(tert-butyl)-9H-carbazol-9-yl)-4-(2-(pyridin-2-yl)phenyl)pyridin-2-yl)phenyl)-9H-carbazol-3-yl)aniline

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(9H-carbazole-3-carbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(3,6-diphenyl-9H-carbazol-9-yl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-((6-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-((6-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3-(tert-butyl)-9H-carbazole)

9,9′-(2,6-bis(dibenzo[b,d]furan-1-yl)-4-(2-(pyridin-4-yl)phenyl)pyridine-3,5-diyl)bis(3-phenyl-9H-carbazole)

9,9′-((3-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(3,1-phenylene))bis(9H-carbazole-3-carbonitrile)

5,5′-(3,6-bis(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

9,9′-((3-(tert-butyl)-9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″-(6-(3-(9H-carbazol-9-yl)phenyl)-4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(3-methyl-9H-carbazole)

9,9′-((3,5-bis(dibenzo[b,d]thiophen-3-yl)-4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(9-phenyl-9H-carbazol-3-yl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-(6-(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(9H-carbazole-3-carbonitrile)

9-(4-(3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)phenyl)-9H-carbazole-3-carbonitrile

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-6-(10H-phenoxazin-10-yl)pyridine-2,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9-(2,5,6-tris(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)-9H-carbazole-3,6-dicarbonitrile

9,9′-((6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3-phenyl-9H-carbazole)

9,9′,9″-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-(o-tolyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

5-(4-(2-(2,6-diphenylpyridin-3-yl)phenyl)-2,6-bis(9-phenyl-9H-carbazol-1-yl)pyridin-3-yl)-5H-pyrido[4,3-b]indole

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-di-o-tolylpyridine-2,5-diyl)bis(4,1-phenylene))bis(3-(tert-butyl)-9H-carbazole)

9,9′-(6-(9-phenyl-9H-carbazol-1-yl)-4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(3-methyl-9H-carbazole)

5,5′,5″-(5-(5H-pyrido[4,3-b]indol-5-yl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,3,6-triyl)tris(5H-pyrido[3,2-b]indole)

9,9′-(6-(dibenzo[b,d]furan-4-yl)-4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,3-diyl)bis(3-methyl-9H-carbazole)

9,9′-(6-(3-methyl-9H-carbazol-9-yl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole)

9,9′-(6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(9H-pyrido[2,3-b]indole)

9,9′-((4-(2-(2,6-dimethylpyridin-3-yl)phenyl)-6-(9-phenyl-9H-carbazol-1-yl)pyridine-2,3-diyl)bis(2,1-phenylene))bis(9H-carbazole-3,6-dicarbonitrile)

5,5′,5″-(6-(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl-4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(5H-pyrido[3,2-b]indole)

5,5′-(2,6-bis(3-phenyl-9H-carbazol-9-yl)-4-(2-(pyridin-2-yl)phenyl)pyridine-3,5-diyl)bis(5H-pyrido[3,2-b]indole)

5,5′,5″-(5-[1,1′-biphenyl]-2-yl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(5H-pyrido[4,3-b]indole)

9,9′-(3,6-bis(dibenzo[b,d]furan-4-yl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(3-phenyl-9H-carbazole)

9,9′-(4-(2-(2,6-dimethylpyridin-3-yl)phenyl)-3,6-bis(3-phenyl-9H-carbazol-9-yl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

1,1′,1″-(5-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,6-triyl)tris(9-phenyl-9H-carbazole)

2-(2-(2,5-di([1,1′:3′,1″-terphenyl]-5′-yl)-3,6-bis(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phenyl)benzo[d]thiazole

9-(3-(4-(2-(6-methylpyridin-2-yl)phenyl-5,6-bis(9-phenyl-9H-carbazol-3-yl)pyridin-2-yl)phenyl)-9H-carbazole-3-carbonitrile

9,9′,9″-((6-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(benzene-4,1-diyl))tris(9H-carbazole)

9,9′-(3-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole)

9,9′-((3-(dibenzo[b,d]thiophen-4-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

N,N-diphenyl-4-(9-(3,5,6-tris(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridin-2-yl)-9H-carbazol-3-yl)aniline

9-(3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)-9H-pyrido[3,4-b]indole

9,9′-(3-(dibenzo[b,d]furan-3-yl)-4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridine-2,6-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-((4(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-diphenylpyridine-2,5-diyl)bis(4,1-phenylene))bis(3,6-di-tert-butyl-9H-carbazole)

4,4′-((4-(2-(pyridin-4-yl)phenyl)-3,5-bis(9H-pyrido[2,3-b]indol-9-yl)pyridine-2,6-diyl)bis(9H-carbazole-9,3-diyl))bis(N,N-diphenylaniline)

9,9′-(3,6-bis(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-pyrido[3,4-b]indole)

9,9′,9″-(6-(dibenzo[b,d]furan-4-yl)-4-(2-(pyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-di-tert-butyl-9H-carbazole)

5-(2,5,6-tris(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)-5H-pyrido[3,2-b]indole

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-2′,6′-diphenyl-[3,4′-bipyridine]-2,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-((3-(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-phenyl-9H-carbazole)

9,9′-((3-(3-methyl-9H-carbazol-9-yl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4-4′-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9-(2,6-bis(4-(3-(4(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-2-yl)phenyl)pyridin-3-yl)-9H-carbazole-3-carbonitrile

9,9′-((3-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2″:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-(5,6-bis(dibenzo[b,d]furan-1-yl)-4-(2-pyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(3-phenyl-9H-carbazole)

9,9′-((3,6-bis(2,6-dimethylphenyl)-4-(2-(4,6-diphenyl-1,3,5-thazin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene)bis(3,6-di-tert-butyl-9H-carbazole)

9-(2,5,6-tris(4-(3-cyano-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)-9H-carbazole-3,6-dicarbonitrile

5-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5,6-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-2-yl)-5H-pyrido[3,2-b]indole

9,9′-((6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-((3-([1,1′:3′,1″-terphenyl]-5′-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-(6-(2-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(3,6-di-tert-butyl-9H-carbazole)

9-(4-(4-(2-(2,6-dimethylpyridin-4-yl)phenyl)-2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-3-yl)phenyl)-9H-carbazole-3-carbonitrile

9,9′,9″-((5-(3-cyano-9H-carbazol-9-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(9H-carbazole-3-carbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-diphenylpyridine-2,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

2-(2-(2,2″,6,6″-tetraphenyl-6′-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)-[4,2′:5′,4″-terpyridin]-4′-yl)phenyl)benzo[d]oxazole

5-(3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)-5H-pyrido[3,2-b]indole

9,9′-(6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,5-diyl)bis(3,6-dimethyl-9H-carbazole)

9,9′-((3-(dibenzo[b,d]furan-3-yl)-4(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-(3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-pyrido[2,3-b]indole)

9,9′-(2,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridine-3,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-diphenylpyridine-2,5-diyl)bis(4,1-phenylene))bis(3-phenyl-9H-carbazole)

4,4′-(9-(6-(2-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridin-2-yl)-9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline)

9,9′-(6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(2,2″,6,6″-tetraphenyl-[4,2′:6′,4″-terpyridin]-4′-yl)phenyl)pyridine-2,5-diyl)bis(3-methyl-9H-carbazole)

5,5′-(2,6-bis(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-3,5-diyl)bis(5H-pyrido[4,3-b]indole)

9-(4-(2,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)phenyl.)-9H-carbazole-3-carbonitrile

9,9′-((3,6-bis(dibenzo[b,d]furan-4-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-25-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

2-(2-(6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)-2,3-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phenyl)benzo[d]thiazole

5-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-2-yl)-5H-pyrido[3,2-b]indole

9,9′,9″-((5-(dibenzo[b,d]furan-4-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

5,5′-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

9-(4-(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridin-3-yl)phenyl)-9H-carbazole-3-carbonitrile

9(4′-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-2,2″,6,6″-terphenyl-[4,2′:6′,4″-terpyridin]-3′-yl)-3-phenyl-9H-carbazole

9,9′-(3,5-bis(4-(3-phenyl-9H-carbazol-9-yl)phenyl)-4-(2-(pyridin-2-yl)phenyl)pyridine-2,6-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′,9″-((5-(2,6-dimethylphenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

9,9′-((4-(2-(4,6-diphenyl)-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9-(3,6-di([1,1′:3′,1″-terphenyl]-2′-yl)-4-(2-(2,6-dimethylpyridin-4-yl)phenyl)pyridin-2-yl)-9H-pyrido[3,4-b]indole

9,9′,9″-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

5-(2,5,6-tris(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-pyridin-4-yl)phenyl)pyridin-3-yl)-5H-benzo[b]carbazole

9,9′-(3-(2-(9H-carbazol-9-yl)phenyl)-4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(3,6-dimethyl-9H-carbazole)

5,5′-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(9-phenyl-9H-carbazol-3-yl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

5-(3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)-5H-pyrido[4,3-b]indole

9,9′,9″-((4-(2(2,6-diphenylpyrimidin-4-yl)phenyl)-5-(o-tolyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

4,4′-(9-(6-(9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyridin-3-yl)phenyl)pyridin-2-yl)-9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline)

9,9′-((2,6-bis(dibenzo[b,d]thiophen-2-yl)-4-(2-(pyridin-3-yl)phenyl)pyridine-3,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-6-(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-pyrido[2,3-b]indole)

9,9′-((6-(9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyridin-4-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-((6-(4-(3-cyano-9H-carbazol-9-yl)phenyl)-4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(2,1-phenylene))bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(9H-carbazole-3,6-dicarbonitrile)

4,4′-((5,6-di([1,1′-biphenyl]-2-yl)-4-(2-(pyridin-3-yl)phenyl)pyridine-2,3-diyl)bis(9H-carbazole-9,3-diyl))bis(N,N-diphenylaniline)

9,9′-((3-(dibenzo[b,d]thiophen-4-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′,9″-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-(o-tolyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3,6-dimethyl-9H-carbazole)

9,9′,9″-((5-(dibenzo[b,d]furan-1-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-6-(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-((4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-2′,6′-diphenyl-[2,4′-bipyridine]-5,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′-((3-([1,1′-biphenyl]-2-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene)bis(3-methyl-9H-carbazole)

5,5′-(4-(2-(4,6-diphenyl-1,3,5-thazin-2-yl)phenyl)-2,6-bis(9-phenyl-9H-carbazol-3-yl)pyridine-3,5-diyl)bis(5H-pyrido[4,3-b]indole)

4,4′-(((6-([1,1′-biphenyl]-2-yl)-4-(2-(benzo[d]oxazol-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(9H-carbazole-9,3-diyl))bis(N,N-diphenylaniline)

5,5′-(6-(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

9-(2-(2,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(6-menthylpyridin-2-yl)phenyl)pyridin-3-yl)phenyl)-9H-carbazole-3,6-dicarbonitrile

9,9′-((6-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene)bis(9H-carbazole)

9,9′-((3-([1,1′:3′,1″-terphenyl]-2′-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-menthyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-3,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3-(4(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3,6-dimethyl-9H-carbazole)

9,9′,9″-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(benzene-4,1-diyl))tris(3-methyl-9H-carbazole)

9,9′-((6-(3,6-dimethyl-9H-carbazol-9-yl)-4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3-diyl)bis(4,1-phenylene)bis(3-phenyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-6-(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-3,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′,9″-(5-(3-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl-4-(2-(pyridin-3-yl)phenyl)pyridine-2,3,6-triyl)tris(3-methyl-9H-carbazole)

9,9′-(4-(2-(benzo[d]thiazol-2-yl)phenyl)-3,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-((3,5-bis(dibenzo[b]furan-1-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-(tert-butyl)-9H-carbazole)

5-(2,5,6-tris(4-(9H-carbazol-9-yl)phenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-3-yl)-5H-pyrido[4,3-b]indole

5,5′-(3,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-4-(2-(2,6-dimethylpyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(5H-pyrido[4,3-b]indole)

9,9′-((3,6-bis(2,6-dimethylphenyl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(4,1-phenylene))bis(3-(tert-butyl)-9H-carbazole)

9-(4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5,6-bis(4-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-2-yl)-9H-carbazole-3-carbonitrile

9-(3-(4-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-5,6-bis(5H-pyrido[3,2-b]indol-5-yl)pyridin-2-yl)phenyl)-9H-carbazole-3,6-dicarbonitrile

9,9′-(5,6-bis(4-(9H-carbazol-9-yl)phenyl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-((3-(dibenzo[b,d]furan-1-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(4,1-phenylene))bis(3-methyl-9H-carbazole)

9,9′-(4-(2-(6-methylpyridin-2-yl)phenyl)-2,6-bis(5H-pyrido[3,2-b]indol-5-yl)pyridine-3,5-diyl)bis(9H-carbazole-3,6-dicarbonitrile)

9,9′-(3,6-bis(dibenzo[b,d]furan-2-yl)-4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-pyrido[3,4-b]indole)

9-(6-(2-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)-4-(2-(6-methylpyridin-2-yl)phenyl)pyridin-2-yl)-9H-carbazole-3-carbonitrile

9,9′-((4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,6-di-o-tolylpyridine-2,5-diyl)bis(4,1-phenylene))bis(3-phenyl-9H-carbazole)

9-(6-(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-4-(2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)pyridin-2-yl)-9H-carbazole-3,6-dicarbonitrile

9,9′-(6-(3-phenyl-9H-carbazol-9-yl)-4-(2-(pyridin-2-yl)phenyl)pyridine-2,5-diyl)bis(9H-carbazole-3-carbonitrile)

9,9′-(6-(4-(3-methyl-9H-carbazol-9-yl)phenyl)-4-(2-(6-phenylpyridin-2-yl)phenyl)pyridine-2,3-diyl)bis(9H-carbazole-3-carbonitrile);and

5,5′-(5,6-bis(3-(tert-butyl)-9H-carbazol-9-yl)-4-(2-(pyridin-4-yl)phenyl)pyridine-2,3-diyl)bis(5H-pyrido[4,3-b]indole)

In some embodiments, the compound of Formula (V) is selected from

In some embodiments, the compound of Formula (V) is selected from

In some embodiments, compounds of Formula (I)-(V) are substituted withdeuterium.

In some embodiments, compounds of Formula (I)-(V) are light emittingmaterials.

In some embodiments, compounds of Formula (I)-(V) are compound capableof emitting delayed fluorescence.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I)-(V) can produce lightin ultraviolet region, the blue, green, yellow, orange, or red region ofthe visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nmto about 600 nm, or about 600 nm to about 700 nm), or near-infraredregion.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I)-(V) can produce lightin the red or orange region of the visible spectrum (e.g., about 620 nmto about 780 nm, about 650 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I)-(V) can produce lightin the orange or yellow region of the visible spectrum (e.g., about 570nm to about 620 nm; about 590 nm, about 570 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I)-(V) can produce lightin the green region of the visible spectrum (e.g., about 490 nm to about575 nm, about 510 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I)-(V) can produce lightin the blue region of the visible spectrum (e.g., about 400 nm to about490 nm; about 475 nm).

Electronic properties of a library of small chemical molecules can becomputed using known ab initio quantum mechanical computations. Forexample, using a time-dependent density functional theory using, as abasis set, the set of functions known as 6-31G* and a Becke,3-parameter, Lee-Yang-Parr hybrid functional to solve Hartree-Fockequations (TD-DFT/B3LYP/6-31G*), molecular fragments (moieties) can bescreened which have HOMOs above a specific threshold and LUMOs below aspecific threshold, and wherein the calculated triplet state of themoieties is above 2.75 eV.

Therefore, for example, a donor moiety (“D”) can be selected because ithas a HOMO energy (e.g., an ionization potential) of greater than orequal to −6.5 eV. An acceptor moiety (“A”) can be selected because ithas, for example, a LUMO energy (e.g., an electron affinity) of lessthan or equal to −0.5 eV. The linker moiety (“L”) can be a rigidconjugated system which can, for example, sterically restrict theacceptor and donor moieties into a specific configuration, therebypreventing the overlap between the conjugated TC system of donor andacceptor moieties.

In some embodiments, the compound library is filtered using one or moreof the following properties:

1. emission near a certain wavelength;

2. calculated triplet state above a certain energy level;

3. ΔE_(ST) value below a certain value;

4. quantum yield above a certain value;

5. HOMO level; and

6. LUMO level.

In some embodiments, the difference between the lowest singlet excitedstate and the lowest triplet excited state at 77K (ΔE_(ST)) is less thanabout 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less thanabout 0.2 eV, or less than about 0.1 eV. In some embodiments, theΔE_(ST) value is less than about 0.09 eV, less than about 0.08 eV, lessthan about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV,less than about 0.04 eV, less than about 0.03 eV, less than about 0.02eV, or less than about 0.01 eV.

In some embodiments, a compound of Formula (I)-(V) exhibits a quantumyield of greater than 25%, such as about 30%, about 35%, about 40%,about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about75%, about 80%, about 85%, about 90%, about 95%, or greater.

Compositions with the Disclosed Compounds

In some embodiments, a compound of Formula (I)-(V) is combined with,dispersed within, covalently bonded to, coated with, formed on, orotherwise associated with, one or more materials (e.g., small molecules,polymers, metals, metal complexes, etc.) to form a film or layer insolid state. For example, the compound of Formula (I)-(V) may becombined with an electroactive material to form a film. In some cases,the compound of Formula (I)-(V) may be combined with a hole-transportpolymer. In some cases, the compound of Formula (I)-(V) may be combinedwith an electron-transport polymer. In some cases, the compound ofFormula (I)-(V) may be combined with a hole-transport polymer and anelectron-transport polymer. In some cases, the compound of Formula(I)-(V) may be combined with a copolymer comprising both hole-transportportions and electron-transport portions. In such embodiments, electronsand/or holes formed within the solid film or layer may interact with thecompound of Formula (I)-(V).

Exemplary Uses of Disclosed Compounds Organic Light-Emitting Diodes

One aspect of the invention relates to use of the compound of Formula(I)-(V) of the invention as a light-emitting material of an organiclight-emitting device. In some embodiments, the compound represented bythe Formula (I)-(V) of the invention may be effectively used as alight-emitting material in a light-emitting layer of an organiclight-emitting device. In some embodiments, the compound of Formula(I)-(V) comprises a delayed fluorescent material emitting delayedfluorescent light (delayed fluorescence emitter). In some embodiments,the invention provides a delayed fluorescence emitter having thestructure of Formula (I)-(V). In some embodiments, the invention relatesto the use of the compound of Formula (I)-(V) as the delayedfluorescence emitter. In some embodiments, the light emitting layercomprises a compound of Formula (I)-(V) as an assist dopant.

In some embodiments, the compound of Formula (I)-(V) can be used as ahost material and used with one or more light-emitting materials, andthe light-emitting material can be a fluorescent material, aphosphorescent material or a TADF material. In some embodiments, thecompound of Formula (I)-(V) can be used as a hole transport material. Insome embodiments, the compound of Formula (I)-(V) can be used as anelectron transport material. In some embodiments, the invention relatesto a method for emitting delayed fluorescent light from the compound ofFormula (I)-(V). In some embodiments, an organic light-emitting devicecomprising the compound as a light-emitting material, emits delayedfluorescent light, and has a high light emission efficiency.

In some embodiments, a light-emitting layer comprises a compound ofFormula (I)-(V), wherein the compound of Formula (I)-(V) is orientedparallel to the substrate. In some embodiments, the substrate is a filmforming surface. In some embodiments, the orientation of the compound ofFormula (I)-(V) with respect to the film forming surface influences ordetermines the propagation directions of the light emitted by thecompound to be aligned. In some embodiments, the alignment of thepropagation directions of the light emitted by the compound of Formula(I)-(V) enhances the light extraction efficiency from the light-emittinglayer.

One aspect of the invention relates to an organic light-emitting device.In some embodiments, the organic light-emitting device comprises alight-emitting layer. In some embodiments, the light-emitting layercomprises a compound of Formula (I)-(V) as a light-emitting material. Insome embodiments, the organic light-emitting device is an organicphotoluminescent device (organic PL device). In some embodiments, theorganic light-emitting device is an organic electroluminescent device(organic EL device). In some embodiments, the compound of Formula(I)-(V) assists the light emission of another light-emitting materialcomprised in the light-emitting layer, i.e., as a so-called assistantdopant. In some embodiments, the compound of Formula (I)-(V) comprisedin the light-emitting layer is in its the lowest excited singlet energylevel, which is comprised between the lowest excited singlet energylevel of the host material comprised in the light-emitting layer and thelowest excited singlet energy level of another light-emitting materialcomprised in the light-emitting layer.

In some embodiments, the organic photoluminescent device comprises atleast one light-emitting layer. In some embodiments, the organicelectroluminescent device comprises at least an anode, a cathode, and anorganic layer between the anode and the cathode. In some embodiments,the organic layer comprises at least a light-emitting layer. In someembodiments, the organic layer comprises only a light-emitting layer. Insome embodiments, the organic layer, comprises one or more organiclayers in addition to the light-emitting layer. Examples of the organiclayer include a hole transporting layer, a hole injection layer, anelectron barrier layer, a hole barrier layer, an electron injectionlayer, an electron transporting layer and an exciton barrier layer. Insome embodiments, the hole transporting layer may be a hole injectionand transporting layer having a hole injection function, and theelectron transporting layer may be an electron injection andtransporting layer having an electron injection function. An example ofan organic electroluminescent device is shown in FIG. 1.

Substrate

In some embodiments, the organic electroluminescent device of theinvention is supported by a substrate, wherein the substrate is notparticularly limited and may be any of those that have been commonlyused in an organic electroluminescent device, for example those formedof glass, transparent plastics, quartz and silicon.

Anode

In some embodiments, the anode of the organic electroluminescent deviceis made of a metal, an alloy, an electroconductive compound, or acombination thereof. In some embodiments, the metal, alloy, orelectroconductive compound has a large work function (4 eV or more). Insome embodiments, the metal is Au. In some embodiments, theelectroconductive transparent material is selected from CuI, indium tinoxide (ITO), SnO₂, and ZnO. In some embodiments, an amorphous materialcapable of forming a transparent electroconductive film, such as IDIXO(In₂O₃—ZnO), is be used. In some embodiments, the anode is a thin film.In some embodiments the thin film is made by vapor deposition orsputtering. In some embodiments, the film is patterned by aphotolithography method. In some embodiments, where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In some embodiments,when a material can be applied as a coating, such as an organicelectroconductive compound, a wet film forming method, such as aprinting method and a coating method is used. In some embodiments, whenthe emitted light goes through the anode, the anode has a transmittanceof more than 10%, and the anode has a sheet resistance of severalhundred Ohm per square or less. In some embodiments, the thickness ofthe anode is from 10 to 1,000 nm. In some embodiments, the thickness ofthe anode is from 10 to 200 nm. In some embodiments, the thickness ofthe anode varies depending on the material used.

Cathode

In some embodiments, the cathode is made of an electrode material ametal having a small work function (4 eV or less) (referred to as anelectron injection metal), an alloy, an electroconductive compound, or acombination thereof. In some embodiments, the electrode material isselected from sodium, a sodium-potassium alloy, magnesium, lithium, amagnesium-cupper mixture, a magnesium-silver mixture, amagnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminummixture, and a rare earth metal. In some embodiments, a mixture of anelectron injection metal and a second metal that is a stable metalhaving a larger work function than the electron injection metal is used.In some embodiments, the mixture is selected from a magnesium-silvermixture, a magnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, a lithium-aluminum mixture, andaluminium. In some embodiments, the mixture increases the electroninjection property and the durability against oxidation. In someembodiments, the cathode is produced by forming the electrode materialinto a thin film by vapor deposition or sputtering. In some embodiments,the cathode has a sheet resistance of several hundred Ohm per square orless. In some embodiments, the thickness of the cathode ranges from 10nm to 5 μm. In some embodiments, the thickness of the cathode rangesfrom 50 to 200 nm. In some embodiments, for transmitting the emittedlight, any one of the anode and the cathode of the organicelectroluminescent device is transparent or translucent. In someembodiments, the transparent or translucent electroluminescent devicesenhances the light emission luminance.

In some embodiments, the cathode is formed with an electroconductivetransparent material, as described for the anode, to form a transparentor translucent cathode. In some embodiments, a device comprises an anodeand a cathode, both being transparent or translucent.

Light-Emitting Layer

In some embodiments, the light-emitting layer is a layer, in which holesand electrons, injected respectively from the anode and the cathode, arerecombined to form excitons. In some embodiments the layer emits light.

In some embodiments, a light-emitting material is solely used as thelight-emitting layer. In some embodiments, the light-emitting layercontains a light-emitting material, and a host material. In someembodiments, the light-emitting material is one or more compounds ofFormula (I)-(V). In some embodiments, for the organic electroluminescentdevice and the organic photoluminescent device to exhibit a high lightemission efficiency, the singlet excitons and the triplet excitonsgenerated in the light-emitting material are confined in thelight-emitting material. In some embodiments, a host material is used inaddition to the light-emitting material in the light-emitting layer. Insome embodiments, the host material is an organic compound. In someembodiments, the organic compounds have excited singlet energy andexcited triplet enemy, at least one of which is higher than those of thelight-emitting material of the invention. In some embodiments, thesinglet excitons and the triplet excitons generated in thelight-emitting material of the invention are confined in the moleculesof the light-emitting material of the invention. In some embodiments,the singlet and triplet excitons are sufficiently confined to elicit thelight emission efficiency. In some embodiments, the singlet excitons andthe triplet excitons are not confined sufficiently, though a high lightemission efficiency is still obtained, and thus a host material capableof achieving a high light emission efficiency can be used in theinvention without any particular limitation. In some embodiments, thelight emission occurs in the light-emitting material of thelight-emitting layer in the devices of the invention. In someembodiments, the emitted light contains both fluorescent light anddelayed fluorescent light. In some embodiments, the emitted lightcomprises emitted light from the host material. In some embodiments, theemitted light consists of emitted light from the host material. In someembodiments, the emitted light light comprises emitted light from acompound of Formula (I)-(V), and emitted light from the host material.In some embodiments, a TADF molecule and a host material are used. Insome embodiments, the TADF is an assistant dopant.

In some embodiments, when a host material is used, the amount of thecompound of the invention as the light-emitting material contained inthe light-emitting layer is 0.1% by weight or more. In some embodiments,when a host material is used, the amount of the compound of theinvention as the light-emitting material contained in the light-emittinglayer is 1% by weight or more. In some embodiments, when a host materialis used, the amount of the compound of the invention as thelight-emitting material contained in the light-emitting layer is 50% byweight or less. In some embodiments, when a host material is used, theamount of the compound of the invention as the light-emitting materialcontained in the light-emitting layer is 20% by weight or less. In someembodiments, when a host material is used, the amount of the compound ofthe invention as the light-emitting material contained in thelight-emitting layer is 10% by weight or less.

In some embodiments, the host material in the light-emitting layer is anorganic compound comprising a hole transporting function and an electrontransporting function. In some embodiments, the host material in thelight-emitting layer is an organic compound that prevents the emittedlight from being increased in wavelength. In some embodiments, the hostmaterial in the light-emitting layer is an organic compound with a highglass transition temperature.

In some embodiments, the host material is selected from e groupconsisting of:

Injection Layer

An injection layer is a layer between the electrode and the organiclayer. In some embodiments, the injection layer decreases the drivingvoltage and enhances the light emission luminance. In some embodiments,the injection layer includes a hole injection layer and an electroninjection layer. The injection layer can be positioned between the anodeand the light-emitting layer or the hole transporting layer, and betweenthe cathode and the light-emitting layer or the electron transportinglayer. In some embodiments, an injection layer is present. In someembodiments, no injection layer is present.

Barrier Layer

A barrier layer is a layer capable of inhibiting charges (electrons orholes) and/or excitons present in the light-emitting layer from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer is between the light-emitting layer and the holetransporting layer, and inhibits electrons from passing through thelight-emitting layer toward the hole transporting layer. In someembodiments, the hole barrier layer is between the light-emitting layerand the electron transporting layer, and inhibits holes from passingthrough the light-emitting layer toward the electron transporting layer.In some embodiments, the barrier layer inhibits excitons from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer and the hole barrier layer are exciton barrierlayers. As used herein, the term “electron barrier layer” or “excitonbarrier layer” includes a layer that has the functions of both electronbarrier layer and of an exciton barrier layer.

Hole Barrier Layer

A hole barrier layer acts as an electron transporting layer. In someembodiments, the hole barrier layer inhibits holes from reaching theelectron transporting layer while transporting electrons. In someembodiments, the hole barrier layer enhances the recombinationprobability of electrons and holes in the light-emitting layer. Thematerial for the hole barrier layer may be the same materials as theones described for the electron transporting layer.

Electron Barrier Layer

As electron barrier layer transports holes. In some embodiments, theelectron barrier layer inhibits electrons from reaching the holetransporting layer while transporting holes. In some embodiments, theelectron barrie layer enhances the recombination probability ofelectrons and holes in the light-emitting layer. Next, preferredexamples of compounds usable as an electron barrier material arementioned below.

Exciton Barrier Layer

An exciton barrier layer inhibits excitons generated throughrecombination of holes and electrons in the light-emitting layer frombeing diffused to the charge transporting layer. In some embodiments,the exciton barrier layer enables effective confinement of excitons inthe light-emitting layer. In some embodiments, the light emissionefficiency of the device is enhanced. In some embodiments, the excitonbarrier layer is adjacent to the light-emitting layer on any of the sideof the anode and the side of the cathode, and on both the sides. In someembodiments, where the exciton barrier layer is on the side of theanode, the layer can be between the hole transporting layer and thelight-emitting layer and adjacent to the light-emitting layer. In someembodiments, where the exciton barrier layer is on the side of thecathode, the layer can be between the light-emitting layer and thecathode and adjacent to the light-emitting layer. In some embodiments, ahole injection layer, an electron barrier layer, or a similar layer isbetween the anode and the exciton barrier layer that is adjacent to thelight-emitting layer on the side of the anode. In some embodiments, ahole injection layer, an electron barrier layer, a hole barrier layer,or a similar layer is between the cathode and the exciton barrier layerthat is adjacent to the light-emitting layer on the side of the cathode.In some embodiments, the exciton barrier layer comprises excited singletenergy and excited triplet energy, at least one of which is higher thanthe excited singlet energy and the excited triplet energy of thelight-emitting material, respectively.

Hole Transporting Layer

The hole transporting layer comprises a hole transporting material. Insome embodiments, the hole transporting layer is a single layer. In someembodiments, the hole transporting layer comprises a plurality oflayers.

In some embodiments, the hole transporting material has one of injectionor transporting property of holes and barrier property of electrons. Insome embodiments, the hole transporting material is an organic material.In some embodiments, the hole transporting material is an inorganicmaterial. Examples of known hole transporting materials that may be usedherein include but are not limited to a triazole derivative, anoxadiazole derivative, an imidazole derivative, a carbazole derivative,an indolocarbazole derivative, a polyaralkane derivative, a pyrazolinederivative, a pyrazolone derivative, a phenylenediamine derivative, anarylamine derivative, an amino-substituted chalcone derivative, anoxazole derivative, a styrylanthracene derivative, a fluorenonederivative, a hydrazone derivative, a stilbene derivative, a silazanederivative, an aniline copolymer and an electroconductive polymeroligomer, particularly a thiophene oligomer, or a combination thereof.In some embodiments, the hole transporting material is selected from aporphyrin compound, an aromatic tertiary amine compound, and astyrylamine compound. In some embodiments, the hole transportingmaterial is an aromatic tertiary amine compound. Next, preferredexamples of compounds usable as a hole transport material are mentionedbelow.

Electron Transporting Layer

The electron transporting layer comprises an electron transportingmaterial. In some embodiments, the electron transporting layer is asingle layer. In some embodiments, the electron transporting layercomprises a plurality of layer.

In some embodiments, the electron transporting material needs only tohave a function of transporting electrons, which are injected from thecathode, to the light-emitting layer. In some embodiments, the electrontransporting material also function as a hole harrier material. Examplesof the electron transporting layer that may be used herein include butare not limited to a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane,an anthrone derivatives, an oxadiazole derivative, an azole derivative,an azine derivative, or a combination thereof, or a polymer thereof. Insome embodiments, the electron transporting material is a thiadiazolederivative, or a quinoxaline derivative. In some embodiments, theelectron transporting material is a polymer material. Next, preferredexamples of compounds usable as an electron transport material arementioned below.

Molecular Weight

The molecular weight of the compound represented by the formula (1) is,for example, in the case of using it by forming an organic layer thatcontains a compound represented by the formula (1) according to a vapordeposition method, preferably 1500 or less, more preferably 1200 orless, even more preferably 1000 or less, still more preferably 900 orless.

Polymer

The compound represented by the formula (1) may be formed into a filmaccording to a coating method irrespective of the molecular weightthereof. According to a coating method, even a compound having arelatively large molecular weight can be formed into a film.

By applying the invention, it may be taken into consideration to use acompound containing plural structures represented by the formula (1) inthe molecule thereof.

For example, a polymerizable group is previously introduced in thestructure represented by the formula (1), and it may be taken intoconsideration to use a polymer obtained through polymerization of thepolymerizable group. For example, a monomer is obtained by replacing anyone of the hydrogen in the structure of formula (1) by a polymerizablefunctional group, and this is homo-polymerized or copolymerized with anyother monomer to give a polymer having a repeating unit. Alternatively,compounds each having a structure represented by the formula (1) arecoupled to give a dimer or a trimer. Examples of the polymer having arepeating unit that contains structure represented by the formula (1)include polymers containing a structure represented by the followingformula (A) or (B).

In the formula (A) and (B), Q represents a group containing thestructure represented by the formula (1), and L¹ and L² each represent alinking group. The carbon number of the linking group is preferably 0 to20, more preferably 1 to 15, even more preferably 2 to 10.

The linking group preferably has a structure represented by —X¹¹-L¹¹-.Here, X¹¹ represents an oxygen atom or a sulfur atom, and is preferablyan oxygen atom; L¹¹ represents a linking group, and is preferably asubstituted or unsubstituted alkylene group or a substituted orunsubstituted arylene group, more preferably a substituted orunsubstituted alkylene group having 1 to 10 carbon atoms or asubstituted or unsubstituted phenylene group.

In the formulae (A) and (B), R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ eachindependently represent a substituent. Preferably, they each are asubstituted or unsubstituted alkyl group having 1 to 6 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, ora halogen atom, more preferably an unsubstituted alkyl group having 1 to3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbonatoms, a fluorine atom or a chlorine atom, and even more preferably anunsubstituted alkyl group having 1 to 3 carbon atoms, or anunsubstituted alkoxy 5 group having 1 to 3 carbon atoms.

The linking group represented by L¹ and L² may be introduced byreplacing any one of the hydrogen in the structure of the formula (1).Two or more linking groups may bond to one Q to form a crosslinkedstructure or a network structure.

Specific structural examples of the repeating unit include structuresrepresented by the following formulae (C) to (F).

Polymers having a repeating unit of the formulae (C) to (F) may besynthesized by replacing any one of the hydrogen by a hydroxy group intoa structure of the formula (1), then introducing a polymerizable groupinto the structure through reaction with any of the following compoundsvia the hydroxy group serving as a linker, and polymerizing thepolymerizable group.

The polymer having a structure represented by the formula (1) may be apolymer containing a repeating unit alone having a structure representedby the formula (1) or may be a polymer containing a repeating unithaving any other structure. The repeating unit having a structurerepresented by the formula (1) contained in the polymer may be one typealone or may contain two or more types of repeating units. A repeatingunit not having a structure represented by the formula (1) includesthose derived from monomers to be used in ordinary copolymerization. Forexample, there are mentioned repeating units derived from monomershaving an ethylenic unsaturated bond such as ethylene, styrene, etc.

In some embodiments, a compound of Formula (I)-(V) is comprised in thelight-emitting layer of a device of the invention. In some embodiments,a compound of Formula (I)-(V) is comprised in the light-emitting layerand at least one other layers. In some embodiments, the compounds ofFormula (I)-(V) are independently selected for each layers. In someembodiments, the compounds of Formula (I)-(V) are the same. In someembodiments, the compounds of Formula (I)-(V) are different. Forexample, the compound represented by the Formula (I)-(V) may be used inthe injection layer, the barrier layer, the hole barrier layer, theelectron barrier layer, the exciton barrier layer, the hole transportinglayer, the electron transporting layer and the like described above. Thefilm forming method of the layers are not particularly limited, and thelayers may be produced by any dry processes and/or wet processes.

Specific examples of materials that can be used in the organicelectroluminescent device are shown above, but the materials that may beused in the invention are not construed as being limited to the examplecompounds. In some embodiments, a material having a particular functioncan also have another function.

Film Forming Method

The compound of the invention may be formed as a film on a substrate byany methods.

Before forming the film, the substrate may be heated or cooled, and thefilm quality and the molecular packing in the film may be controlled bychanging the temperature of the substrate. The temperature of thesubstrate is not particularly limited, and is preferably in a range offrom 0 to 200° C., more preferably in a range of from 15 to 100° C., andparticularly preferably in a range of from 20 to 95° C.

Before forming a film of the compound of the invention on a substrate,the film may be formed by a vacuum process or a solution process, bothof which are preferred.

Specific examples of the film formation by a vacuum process include aphysical vapor deposition, such as vacuum deposition, sputtering method,ion plating method and molecular beam epitaxy (MBE), and chemical vapordeposition (CVD), such as plasma polymerization, and vacuum depositionis preferably used.

The film formation by a solution process means a method, in which anorganic compound is dissolved in a solvent capable of dissolving thesame, and a film is formed by using the resulting solution. Specificexamples thereof used include ordinary methods, for example, a coatingmethod, such as a casting method, a dip coating method, a die coatermethod, a roll coater method, a bar coater method and a spin coatingmethod, a printing method, such as ink-jet method, screen printingmethod, gravure printing method, flexography printing method, offsetprinting method and microcontact printing method, and Langmuir-Blodgett(LB) method, and casting method, spin-coating method, preferably ink-jetmethod, gravure printing method, flexography printing, method, offsetprinting method and microcontact printing method are used.

The coating solution for an organic semiconductor device of theinvention capable of being used for film formation by a solution processwill be described below.

In the case where the film is formed on a substrate by a solutionprocess, the material for forming the layer may be dissolved ordispersed in a suitable organic solvent (for example, a hydrocarbonsolvent, such as hexane, octane, decane, toluene, xylene, mesitylene,ethylberizene, decalin and 1-methylnaphthalene, a ketone solvent, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone andcyclohexanone, a halogenated hydrocarbon solvent, such asdichloromethane, chloroform, tetrachloromethane, dichloroethane,trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene andchlorotoluene, an ester solvent, such as ethyl acetate, butyl acetateand amyl acetate, an alcohol solvent, such as methanol, ethanol,propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve,ethyl cellosolve and ethylene glycol, an ether solvent, such as diethylether, dibutyl ether, tetrahydrofuran, dioxane and anisole, an amide orimide solvent, such as N,N-dimethylformamide, N,N-dimethylacetamide,1-methyl-2-pyrrolidone and 1-methyl 2-imidazolidinone, a sulfoxidesolvent, such as dimethylsulfoxide, and a nitrile solvent, such asacetonitrile) and/or water to prepare a coating liquid, which may bethen coated by various coating methods to form the thin film.

Devices

In some embodiments, the compounds of the disclosure are incorporatedinto a device. For example, the device includes, but is not limited toan OLED bulb, an OLED lamp, a television screen, a computer monitor, amobile phone, and a tablet.

In some embodiments, an electronic device comprises an OLED comprisingan anode, a cathode, and at least one organic layer comprising a lightemitting layer between the anode and the cathode, wherein the lightemitting layer comprises

a host material; and

a compound of Formula (I)-(V).

In some embodiments, the light emitting layer comprises a compound ofFormula (I)-(V) as a light emitting material.

In some embodiments, the light emitting layer comprises a compound ofFormula (I)-(V) as an assist dopant.

In some embodiments, the light emitting layer of the OLED furthercomprises a fluorescent material wherein the compound of Formula (I)-(V)converts triplets to singlets for the fluorescent emitter.

In some embodiments, compositions described herein may be incorporatedinto various light-sensitive or light-activated devices, such as a OLEDsor photovoltaic devices. In some embodiments, the composition may beuseful in facilitating charge transfer or energy transfer within adevice and/or as a hole-transport material. The device may be, forexample, an organic light-emitting diode (OLED), an organic integratedcircuit (O-IC), an organic field-effect transistor (O-FET), an organicthin-film transistor (O-TFT), an organic light-emitting transistor(O-LET), an organic solar cell (O-SC), an organic optical detector, anorganic photoreceptor, an organic field-quench device (O-FQD), alight-emitting electrochemical cell (LEC) or an organic laser diode(O-laser).

Bulbs or Lamps

In some embodiments, an electronic device comprises an OLED comprisingan anode, a cathode, and at least one organic layer comprising a lightemitting layer between the anode and the cathode, wherein the lightemitting layer comprises

a host material;

a compound of Formula (I)-(V);

wherein the compound of Formula (I)-(V) is a light emitting material;and

an OLED driver circuit.

In some embodiments, the light emitting lays r comprises a compound ofFormula (I)-(V) as an assist dopant.

In some embodiments, a device comprises OLEDs that differ in color. Insome embodiments, a device comprises an array comprising a combinationof OLEDs. In some embodiments, the combination of OLEDs is a combinationof three colors (e.g., RGB). In some embodiments, the combination ofOLEDs is a combination of colors that are not red, green, or blue (forexample, orange and yellow green). In some embodiments, the combinationof OLEDs is a combination of two, four, or more colors.

In some embodiments, a device is an OLED light comprising:

a circuit board having a first side with a mounting surface and anopposing second side, and defining at least one aperture;

at least one OLED on the mounting surface, the at least one OLEDconfigured to emanate light, comprising:

-   -   an anode, a cathode, and at least one organic layer comprising a        light emitting layer between the anode and the cathode, wherein        the light emitting layer comprises    -   a host material:    -   a compound of Formula (I)-(V);    -   wherein the compound of Formula (I)-(V) light emitting material;

a housing for the circuit board; and

at least one connector arranged at an end of the housing, the housingand the connector defining a package adapted for installation in a lightfixture.

In some embodiments, the light emitting layer comprises a compound ofFormula (I)-(V) as an assist dopant.

In some embodiments, the OLED light comprises a plurality of OLEDsmounted on a circuit board such that light emanates in a plurality ofdirections. In some embodiments, a portion of the light emanated in afirst direction is deflected to emanate in a second direction. In someembodiments, a reflector is used to deflect the light emanated in afirst direction.

Displays or Screens

In some embodiments, the compounds of Formula (I)-(V) can be used in ascreen or a display. In some embodiments, the compounds of Formula(I)-(V) are deposited onto a substrate using a process including, butnot limited to, vacuum evaporation, deposition, vapor deposition, orchemical vapor deposition (CVD). In some embodiments, the substrate is aphotoplate structure useful in a two-sided etch provides a unique aspectratio pixel. The screen (which may also be referred to as a mask) isused in a process in the manufacturing of OLED displays. Thecorresponding artwork pattern design facilitates a very steep and narrowtie-bar between the pixels in the vertical direction and a large,sweeping bevel opening in the horizontal direction. This allows theclose patterning of pixels needed for high definition displays whileoptimizing the chemical deposition onto a TFT backplane.

The internal patterning of the pixel allows the construction of a3-dimensional pixel opening with varying aspect ratios in the horizontaland vertical directions. Additionally, the use of imaged “stripes” orhalftone circles within the pixel area inhibits etching in specificareas until these specific patterns are undercut and fall off thesubstrate. At that point the entire pixel area is subjected to a similaretch rate but the depths are varying depending on the halftone pattern.Varying the size and spacing of the halftone pattern allows etching tobe inhibited at different rates within the pixel allowing for alocalized deeper etch needed to create steep vertical bevels.

A preferred material for the deposition mask is invar. Invar is a metalalloy that is cold rolled into long thin sheet in a steel mill. Invarcannot be electrodeposited onto a rotating mandrel as the nickel mask. Apreferred and more cost feasible method for forming the open areas inthe mask used for deposition is through a wet chemical etching.

In some embodiments, a screen or display pattern is a pixel matrix on asubstrate. In some embodiments, a screen or display pattern isfabricated using lithography (e.g., photolithography and e-beamlithography). In some embodiments, a screen or display pattern isfabricated using a wet chemical etch. In further embodiments, a screenor display pattern is fabricated using plasma etching.

Methods of Manufacturing Devices Using the Disclosed Compounds

An OLEO display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

An OLED display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

In another aspect, provided herein is a method of manufacturing anorganic light-emitting diode (OLED) display, the method comprising:

forming a barrier layer on a base substrate of mother panel;

forming a plurality of display units in units of cell panels on thebarrier layer;

forming an encapsulation layer on each of the display units of the cellpanels;

applying an organic film to an interface portion between the cellpanels.

In some embodiments, the barrier layer is an inorganic film formed of,for example, SiNx, and an edge portion of the harrier layer is coveredwith an organic film formed of polyimide or acryl. In some embodiments,the organic film helps the mother panel to be softly cut in units of thecell panel.

In some embodiments, the thin film transistor (TFT) layer includes alight-emitting layer, a gate electrode, and a source/drain electrode.Each of the plurality of display units may include a thin filmtransistor (TFT) layer, a planarization film formed on the TFT layer,and a light-emitting unit formed on the planarization film, wherein theorganic film applied to the interface portion is formed of a samematerial as a material of the planarization film and is formed at a sametime as the planarization film is formed. In some embodiments, alight-emitting unit is connected to the TFT layer with a passivationlayer and a planarization film therebetween and an encapsulation layerthat covers and protects the light-emitting unit. In some embodiments ofthe method of manufacturing, the organic film contacts neither thedisplay units nor the encapsulation layer.

Each of the organic film and the planarization film may include any oneof polyimide and acryl. In some embodiments, the barrier layer may be aninorganic film. In some embodiments, the base substrate may be formed ofpolyimide. The method may further include, before the forming of thebarrier layer on one surface of the base substrate formed of polyimide,attaching a carder substrate formed of a glass material to anothersurface of the base substrate, and before the cutting along theinterface portion, separating the carrier substrate from the basesubstrate. In some embodiments, the OLED display is a flexible display.

In some embodiments, the passivation layer is an organic film disposedon the layer to cover the TFT layer. In some embodiments, theplanarization film is an organic film formed on the passivation layer.In some embodiments, the planarization film is formed of polyimide oracryl, like the organic film formed on the edge portion of the barrierlayer. In some embodiments, the planarization film and the organic filmare simultaneously formed when the OLED display is manufactured. In someembodiments, the organic film may be formed on the edge portion of thebarrier layer such that a portion of the organic film directly contactsthe base substrate and a remaining portion of the organic film contactsthe barrier layer while surrounding the edge portion of the barrierlayer.

In some embodiments, the light-emitting layer includes a pixelelectrode, a counter electrode, and an organic light-emitting layerdisposed between the pixel electrode and the counter electrode. In someembodiments, the pixel electrode is connected to the source drainelectrode of the TFT layer.

In some embodiments, when a voltage is applied to the pixel electrodethrough the TFT layer, an appropriate voltage is formed between thepixel electrode and the counter electrode, and thus the organiclight-emitting layer emits light, thereby forming an image. Hereinafter,an image forming unit including the TFT layer and the light-emittingunit is referred to as a display unit.

In some embodiments, the encapsulation layer that covers the displayunit and prevents penetration of external moisture may be formed to havea thin film encapsulation structure in which an organic film and aninorganic film are alternately stacked. In some embodiments, theencapsulation layer has a thin film encapsulation structure in which aplurality of thin films are stacked. In some embodiments, the organicfilm applied to the interface portion is spaced apart from each of theplurality of display units. In some embodiments, the organic film isformed such that a portion of the organic film directly contacts thebase substrate and a remaining portion of the organic film contacts thebarrier layer while surrounding an edge portion of the barrier layer.

In one embodiment, the OLED display is flexible and uses the soft basesubstrate formed of polyimide. In some embodiments, the base substrateis formed on a carrier substrate formed of a glass material, and thenthe carrier substrate is separated.

In some embodiments, the barrier layer is formed on a surface of thebase substrate opposite to the carrier substrate. In one embodiment, thebarrier layer is patterned according to a size of each of the cellpanels. For example, while the base substrate is formed over the entiresurface of a mother panel, the barrier layer is formed according to asize of each of the cell panels, and thus a groove is formed at aninterface portion between the barrier layers of the cell panels. Each ofthe cell panels can be cut along the groove.

In some embodiments, the method of manufacture further comprises cuttingalong the interface portion, wherein a groove is formed in the barrierlayer, wherein at least a portion of the organic film is formed in thegroove, and wherein the groove does not penetrate into the basesubstrate. In some embodiments, the TFT layer of each of the cell panelsis formed, and the passivation layer which is an inorganic film and theplanarization film which is an organic film are disposed on the TFTlayer to cover the TFT layer. At the same time as the planarization filmformed of, for example, polyimide or acryl is formed, the groove at theinterface portion is covered with the organic film formed of, forexample, polyimide or acryl. This is to prevent cracks from occurring byallowing the organic film to absorb an impact generated when each of thecell panels is cut along the groove at the interface portion. That is,if the entire barrier layer is entirely exposed without the organicfilm, an impact generated when each of the cell panels is cut along thegroove at the interface portion is transferred to the barrier layer,thereby increasing the risk of cracks. However, in one embodiment, sincethe groove at the interface portion between the barrier layers iscovered with the organic film and the organic film absorbs an impactthat would otherwise be transferred to the barrier layer, each of thecell panels may be softly cut and cracks may be prevented from occurringin the barrier layer. In one embodiment, the organic film covering thegroove at the interface portion and the planarization film are spacedapart from each other. For example, if the organic film and theplanarization film are connected to each other as one layer, sinceexternal moisture may penetrate into the display unit through theplanarization film and a portion where the organic film remains, theorganic film and the planarization film are spaced apart from each othersuch that the organic film is spaced apart from the display unit.

In some embodiments, the display unit is formed by forming thelight-emitting unit, and the encapsulation layer is disposed on thedisplay unit to cover the display unit. As such, once the mother panelis completely manufactured, the carrier substrate that supports the basesubstrate is separated from the base substrate. In some embodiments,when a laser beam is emitted toward the carrier substrate, the carriersubstrate is separated from the base substrate due to a difference in athermal expansion coefficient between the carrier substrate and the basesubstrate.

In some embodiments, the mother panel is cut in units of the cellpanels. In some embodiments, the mother panel is cut along an interfaceportion between the cell panels by using a cutter. In some embodiments,since the groove at the interface portion along which the mother panelis cut is covered with the organic film, the organic film absorbs animpact during the cutting. In some embodiments, cracks may be preventedfrom occurring in the barrier layer during the cutting.

In some embodiments, the methods reduce a defect rate of a product andstabilize its quality.

Another aspect is an OLED display including: a barrier layer that isformed on a base substrate; a display unit that is formed on the barrierlayer; an encapsulation layer that is formed on the display unit; and anorganic film that is applied to an edge portion of the barrier layer.

EXAMPLES

An embodiment of the present disclosure provides the preparation ofcompounds of Formula (I)-(V) according to the procedures of thefollowing example(s), using appropriate materials. Those skilled in theart will understand that known variations of the conditions andprocesses of the following preparative procedures can be used to preparethese compounds. Moreover, by utilizing the procedures described indetail, one of ordinary skill in the art can prepare additionalcompounds of the present disclosure.

General Information on Analytical Methods

The features of the invention will be described more specifically withreference to examples below. The materials, processes, procedures andthe like shown below may be appropriately modified unless they deviatefrom the substance of the invention. Accordingly, the scope of theinvention is not construed as being limited to the specific examplesshown below. The characteristics of samples were evaluated by using NMR(Nuclear Magnetic Resonance 500 MHz, produced by Bruker), LC/MS (LiquidChromatography Mass Spectrometry, produced by Waters), AC3 (produced byRIKEN KEIKI), High-performance UV/Vis/NIR Spectrophotometer (Lambda 950,produced by PerkinElmer, Co., Ltd.), Fluorescence Spectrophotometer(FluoroMax-4, produced by Horiba, Ltd.), Photonic multichannel analyzer(PMA-12 C10027-01, produced by Hamamatsu Photonics K.K.), Absolute PLQuantum Yield Measurement System (C11347, produced by HamamatsuPhotonics K.K.), Automatic Current voltage brightness measurement system(ETS-170, produced by System engineers co ltd), Life Time MeasurementSystem (EAS-26C, produced by System engineers co ltd), and Streak Camera(Model C4334, produced by Hamamatsu Photonics K.K.).

Example 1

The principle of the features may be described as follows for an organicelectroluminescent device as an example.

In an organic electroluminescent device, carriers are injected from ananode and a cathode to a light-emitting material to form an excitedstate for the light-emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescent device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy utilization. However, the excited triplet statehas a long lifetime and thus causes saturation of the excited state anddeactivation of energy through mutual action with the excitons in theexcited triplet state, and therefore the quantum yield ofphosphorescence may generally be often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescentdevice. In the case where a delayed fluorescent material is used in anorganic electroluminescent device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited singlet state hasthe same wavelength as fluorescent light since it is light emission fromthe excited singlet state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited singlet state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.

Example 2

The compounds of the invention can be synthesized by any method known toone of ordinary skills in the art. The compounds are synthesized fromthe commonly available starting material. The various moieties can beassembled via linear or branched synthetic routes.

Compound 1

A mixture of K₂CO₃ (2.26 g, 16.36 mmol) and 9H-Carbazole (1.83 g, 10.95mmol) in NMP (30 mL) was stirred at r.t. for 1 h and then compound A(1.0 g, 2.18 mmol) was added. The mixture was stirred at 100° C. for 16h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and recrystallized from toluene/MeOH togive compound 1 (2.00 g, 1.91 mmol) in 88% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.53(d, J=8.5 Hz, 4H), 7.97 (d, J=8.5 Hz,2H), 7.74 (d, J=7.5 Hz, 4H), 7.66-7.64 (m, 4H), 7.53-7.43 (m, 6H), 7.38(d, J=8.0 Hz, 4H), 7.06-7.02 (m, 8H), 6.97-6.94 (m, 12H), 6.84 (d, J=8.5Hz, 2H).

MS (ASAP): 1046.7(M+). Calcd for C₇₄H₄₆N₈: 1046.4.

Compound 2

A mixture of K₂CO₃ (2.71 g, 19.6 mmol) and 9H-Carbazole (2.19 g, 13.0mmol) NMP (30 mL) was stirred at r.t. for 1 h and then compound B (1.20g, 2.61 mmol) was added. The mixture was stirred at 100° C. for 16 h.The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH and purified by silica gel columnchromatography (hexane: CHCl3=7:3) to give compound 2 (2.49 g, 2.37mmol) in 90% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.23(d, J=7.5 Hz, 4H), 8.16-8.13 (in, 2H),7.74 (t, J=7.5 Hz, 4H), 7.61-7.39 (m, 14H), 7.13 (d, J=7.5 Hz. 2H),7.06-6.90 (m, 16H), 6.86 (t, J=7.5 Hz, 2H), 6.78 (d, J=7.5 Hz, 1H), 6.71(t, J=7.5 Hz, 1H).

MS (ASAP); 1046.5(M+) Calcd for C₇₄H₄₆N₈: 1046.4,

Compound 3

A mixture of K₂CO₃ (0.67 g, 4.90 mmol) and 3,6-Dimethylcarbazole (0.64g, 3.27 mmol) in NMP (10 mL) was stirred at r.t. for 1 h and thencompound B (03 g, 0.65 mmol) was added. The mixture was stirred at 130°C. for 16 h. The reaction mixture was quenched with H₂O. Theprecipitated products were filtered, washed with MeOH and purified bysilica gel column chromatography (hexane: CHCl3=2:1) to give compound 3(0.48 g, 0.41 mmol) in 63% yield as white powder.

¹H-NMR (50 MHz, CDCl₃, δ): 8.35(dd, J=8.0, 1.0 Hz, 4H), 8.05(dt, J=8.0,1.0 Hz, 1H), 7.95(t, J=8.0 Hz. 1H), 7.56-7.44(m, 10H), 7.35-7.22(m, 8H),7.00(d, J=8.0 Hz, 2H), 6.87(d, J=8.0 Hz, 2H), 6.80-6.70(m, 8H), 6.65 (t,J=7.5 Hz, 1H), 6.58 (d, J=7.5 Hz, 1H), 2.35-2,33 (s, 12H), 2.27 (s, 6H),2.05 (s, 6H).

MS (ASAP): 1158.5(M+). Calcd for C₈₂H₆₂N₈: 1158.5.

Compound 4

A mixture of K₂CO₃ (0.90 g, 6.54 mmol) and 9H-Carbazole (0.73 g, 4.36mmol) in NMP (15 mL) was stirred at r.t. for 1 h and then compound C(0,40 g, 0.87 mmol) was added. The mixture was stirred at 160° C. for 50h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and purified by silica gel columnchromatography to (hexane: toluene=2:1) to give compound 4 (0.50 g, 0.48mmol) in 55% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.74 (dd, J=7.5, 1.0 Hz, 2H), 8.15 (dd,J=7.5, 1.0 Hz, 2H), 7.69-7.62 (m, 8H), 7.52-7.49 (m, 3H), 7.43-7.31 (m,8H), 7.10-6.81 (m, 16H), 6.78 (t, J=7.5 Hz, 1H), 6.72 (t, J=7.5 Hz, 2H),6.52 (t, J=7.5 Hz, 2H), 6.35 (t, J=7.5 Hz, 2H).

MS (ASAP): 1046.3(M+), Calcd for C₇₄H₄₆N₈: 1046.4,

Compound 5

A mixture of K₂CO₃ (0.79 g, 5.72 mmol) and 3,6-Dimethylcarbazole (0.74g, 3.81 mmol) in NMP (15 mL) was stirred at r.t. for 1 h and thencompound C (0.35 g, 0.76 mmol) was added. The mixture was stirred at190° C. for 27 h. The reaction mixture was quenched with H₂O. Theprecipitated products were filtered, washed with MeOH and purified bysilica gel column chromatography (hexane:toluene=1:1) to give compound 5(0.42 g, 0.36 mmol) in 47% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.72(d, J=7.5 Hz, 2H), 8.24(d, J=7.5 Hz,2H), 7.64-7.41(m, 13H), 7.20-7.10 (m, 6H), 7.00-6.88 (m, 5H), 6.70-6.63(m, 6H), 6.51 (d, J=7.5 Hz, 2H), 6.18 (d, J=7.5 Hz, 2H), 2.33 (s, 6H),2.28 (s, 12H), 1.83 (s, 6H).

MS (ASAP): 1158.2(M+), Calcd for C₈₂H₆₂N₈: 1158.5,

Compound 6

A mixture of K₂CO₃ (1.70 g, 12.3 mmol) and 9H-Carbazole (1.37 g, 8.20mmol) in NMP (20 mL) was stirred at r.t. for 1 h and then compound D(0.75 g, 1.64 mmol) was added. The mixture was stirred at 100° C. for 66h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and purified by silica gel columnchromatography to (hexane: CHCl3=2:1) to give compound 6 (1.52 g, 1.45mmol) in 88% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.48-8.46 (m. 2H), 8.09-8.06 (m, 2H), 7.75(d, J=7.5 Hz, 4H), 7.67-7.65 (m, 4H), 7.53-7.39 (m, 13H), 7.06-6.94 (m,20H), 6.79 (d, J=8.5 Hz, 2H).

MS (ASAP): 1045.5(M+). Calcd for C₇₅H₄₇N₇: 1045.4.

Compound 7

A mixture of K₂CO₃ (1.13 g, 8.19 mmol) and 9H-Carbazole (0.91 g, 5.46mmol) in NMP (15 mL) was stirred at r.t. for 1 h and then compound E(0.50 g, 1.09 mmol) was added. The mixture was stirred at 100° C. for 96h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and purified by silica gel columnchromatography to (hexane:toluene=2:1) to give compound 7 (1.11 g, 1.06mmol) in 97% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.38-8.36 (m, 2H), 7.81-7.79 (m, 3H), 7.76(d, J=7.5 Hz, 4H) 7.60-7.58 (m, 4H), 7.51-7.40 (m, 11H), 7.10-6.89 (m,20H), 6.70-6.65 (m, 3H).

MS (ASAP): 1045.2(M+). Calcd for C₇₅H₄₇N₇: 1045.4.

Compound 8

A mixture of K₂CO₃ (1.08 g, 7.87 mmol) and 9H-Carbazole (0.87 g, 5.25mmol) in NMP (10 mL) was stirred at r.t. for 1 h and then2,3,5,6-tetrafluoro-4-[4-(trifluoromethyl)phenyl]pyridine (0.31 g, 1.05mmol) was added. The mixture was stirred at 100° C. for 37 h. Thereaction mixture was quenched with H₂O. The precipitated products werefiltered, washed with MeOH to give compound 8 (0.60 g, 0.67 mmol) in 64%yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 7.75 (d, J=8.0 Hz, 4H), 7.66 (d, J=8.0 Hz,4H), 7.41(d, J=8.0 Hz, 4H), 7.04(dt, J=8.0, 1.0 Hz, 4H), 7.00-6.91 (m,16H), 6.70 (d, J=8.5 Hz, 2H), 6.61 (d, J=8.5 Hz, 2H).

MS (ASAP): 883.3(M+). Calcd for C₆₀H₃₆F₃N₅: 883.3.

Compound 9

Compound 9

A mixture of K₂CO₃ (4.12 g, 29.7 mmol) and 9H-Carbazole (3.32 g, 19.8mmol) in NMP (20 mL) was stirred at r.t. for 1 h and then compound G(1.00 g, 3.97 mmol) was added. The mixture was stirred at 120° C. for 24h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and purified by silica gel columnchromatography (hexane: CHCl3=1:1) to give compound 9 (2.99 g, 3.55mmol) in 89.5% yield as white powder.

¹H -NMR (500 MHz, CDCl₃, δ):7.75(d, J=8.0 Hz, 4H), 7.67(d, J=8.0 Hz,4H), 7.40(d, J=8.0 Hz, 4H), 7.06(t, J=8.0 Hz, 4H), 7.01-6.89(m, 16H),6.75(d, J=8.0 Hz, 2H), 6.61(d, J=8.0 Hz, 2H).

MS (ASAP): 840.4 (M+). Calcd for C₆₀H₃₆N₆: 840.3.

Compound 10

A mixture of K₂CO₃ (1.64 g, 11.8 min) and 9H-Carbazole (1.32 g, 7.93mmol) in NMP (20 mL) was stirred at r.t. for 1 h and then compound H(0.40 g, 1.58 mmol) was added. The mixture was stirred at 100° C. for 96h. The reaction mixture was quenched with H₂O. The precipitated productswas filtered, washed with MeOH and purified by silica gel columnchromatography (hexane:CHCl₃=1:1) to give compound 10 (0.48 g 0.57 mmol)in 36% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 7.77 (d, J=7.5 Hz, 4H), 7.68 (d, J=7.5 Hz,4H), 7.46-7.40(m, 4H), 7.06 (t, J=7.5 Hz, 4H), 7.13-6.84 (m, 17H),6.71-6.67 (m, 2H), 6.56 (t, J=7.5 Hz, 1H).

MS (ASAP): 840.3 (M+). Calcd for C₆₀H₃₆N₆: 840.3.

Compound 11

A mixture of K₂CO₃ (2.46 g, 17.8 mmol) and 9H-Carbazole (1.99 g, 11.9)in NMP (30 mL) was stirred at r.t. for 1 h and then compound I (0.60 g,2.38 mmol) was added. The mixture was stirred at 100° C. for 24 h. Thereaction mixture was quenched with H₂O. The precipitated products werefiltered, washed with MeOH and purified by silica gel columnchromatography (hexane:toluene 1:2) to give compound 11 (1.80 g, 2.14mmol) in 90% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 7.77-7.70 (m, 4H), 7,68-7.65 (m, 2H),7.63-7.56(m, 4H), 7.28-7.22 (m, 4H), 7.10-6.98 (m, 12H), 6.95-6.74 (m,10H).

MS (ASAP): 840.1 (M+). Calcd for C₆₀H₃₆N₆: 840.3.

Compound 12

A mixture of K₂CO₃ (1.49 g, 10,81 mmol) and 9H-Carbazole (1.21 g, 7.21mmol) in NMP (15 mL) was stirred at r.t. for 1 h and then compound J(0.45 g, 0.98 mmol) was added. The mixture was stirred at 130° C. for 75h. The reaction mixture was quenched with H₂O. The precipitated productswere filtered, washed with MeOH, and recrystallized from CHCl₃/MeOH togive compound 12 (0.748 g, 0.714 mmol) in 72.8% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.53(d, J=7.5 Hz, 4H), 8.03(d, J=7.5 Hz,2H), 8.01(d, J=7.5 Hz, 2H), 7.72(d, J=7.5 Hz, 2H), 7.61(d, J=7.5 Hz,2H), 7.53-7.50(m, 2H), 7.48-7.44(m, 8H), 7.39 (d, J=7.5 Hz, 2H), 7.32(dt, J=7.5, 1.0 Hz, 2H), 7.22 (t, J=7.5 Hz, 2H), 7.02-6.99(m, 4H),6.94-6.88(m, 10H), 6.80 (t, J=7.5 Hz, 2H), 6.63 (t, J=7.5 Hz, 2H).

MS (ASAP): 1046.6(M+).Calcd for C₇₄H₄₆N₈: 1046.4,

Compound 13

A mixture of K₂CO₃ (0.90 g, 6.54 mmol) and 3,6-Dimethyl-Carbazole (0.85g, 4.36 mmol) in NMP (10 mL) was stirred at r.t. for 1 h and thencompound J (0.40 g, 0.87 mmol) was added. The mixture was stirred at130° C. for 19 h. The reaction mixture was quenched with H₂O. Theprecipitated products were filtered, washed with MeOH, and purified bysilica gel column chromatography (hexane:toluene=1:1) to give compound13 (0.42 g, 0.36 mmol) in 41.6% yield as white powder.

¹H-NMR (500 MHz, CDCl₃, δ): 8.57(dd, J=7.5, 1.5 Hz, 4H), 8.01(d, J=7.5Hz, 2H), 7.75(s, 2H), 7.55-7.46(m, 8H), 7.36(s, 2H), 7.29-7.25(m, 4H),7.16(s, 2H), 7.05(dd, J=7.5, 1.5 Hz, 2H), 6.88(d, J=7.5 Hz, 2H), 6.81(d,J=7.5 Hz, 2H), 6.79(d, J=7.5 Hz, 2H), 6.71(dd, J=7.5, 1.5 Hz, 2H),6.66(dd, J=7.5, 1.5 Hz, 2H), 6.45(dd, J=7.5, 1.5 Hz, 2H), 2.43 (s, 6H),2.31 (s, 6H), 2.26 (s, 6H), 2.21 (s, 6H),

MS (ASAP): 1158.9(M+), Calcd for C₈₂H₆₂N₈: 1158.5.

Example 3 Preparation of Neat Films

In this example, the compound 1 synthesised in Example 2 wasvapor-deposited on a quartz substrate by a vacuum vapor depositionmethod under a condition of a vacuum degree of 10⁻³ Pa or less, so as toform a thin film having a thickness of 70 nm.

Preparation of Doped Films

The compound 1 and host were also vapor-deposited from a separate vapordeposition source on a quartz substrate by vacuum vapor depositionmethod under a condition of a vacuum degree of 10⁻³ Pa or less, so as toform a thin film having a thickness of 100 nm and a concentration of thecompound 1 of 20% by weight.

Evaluation of the Optical Properties

The samples were irradiated with light having a wavelength of 300 nm at300 K, and thus the light emission spectrum was measured and designatedas fluorescence. The spectrum at 77K was also measured and designated asphosphorescence. The lowest singlet energy (S₁) and the lowest tripletenergy (T₁) was estimated from the onset of fluorescence andphosphorescence spectrum respectively. ΔE_(ST) was calculated from theenergy gap between S₁ and T₁. PLQY was also measured by excitation light300 nm. The time resolved spectrum was obtained by excitation light 337nm with Streak Camera, and the component with a short light emissionlifetime was designated as fluorescent light, whereas the component witha long light emission lifetime was designated as delayed fluorescentlight. The lifetimes of the fluorescent light component (τ_(prompt)) anddelayed fluorescent light component were calculated from the decaycurves.

Preparation and Measurement of OLEDs

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 50 nm, by avacuum vapor deposition method at a vacuum degree of 1.0×10⁻⁴ Pa orless. Firstly, HAT-CN was formed to a thickness of 60 nm on ITO, andthereon TrisPCz was formed to a thickness of 30 nm. mCBP was formed to athickness of 5 nm, and thereon compound 1 and host were thenvapor-co-deposited from separate vapor deposition sources to form alayer having a thickness of 30 nm, which was designated as a lightemitting layer. At this time, the concentration of compound 1 was 30% byweight. SF3-TRZ was then formed to a thickness of 5 mm, and thereonSF3-TRZ and Liq were vapor-co-deposited to a thickness of 30 nm. Liq wasthen vacuum vapor-deposited to a thickness of 2 nm, and then aluminum(Al) was vapor-deposited to a thickness of 100 nm to form a cathode,thereby producing organic electroluminescent devices and measured itsphotoelectrical properties.

The results of the same evaluation with compound 2-11 synthesized inExamples 2, instead of the compound 1 are also measured.

Optical properties doped film (20% TADF: host) PLQY compound host λ em(PL) (in N₂) ΔEst 1 PYD2 480 nm 82% 0.14 eV 2 PYD2 452 nm 32% 0.26 eV 3PYD2 475 nm 77% 0.23 eV 4 PYD2 476 nm 68% 0.17 eV 5 PYD2 495 nm 79% N.O. * 6 DPEPO 473 nm 81% 0.22 eV 7 DPEPO 454 nm 35% 0.23 eV 8 DPEPO 463nm 73% 0.19 eV 9 DPEPO 470 nm 75% 0.13 eV 10 DPEPO 470 nm 80% 0.17 eV *Not observed

device properties @ 1000 nit EML compound concentration host λ em (EL)EQE structure 1 30 wt % PYD2 487 nm 14.3% *1 3 30 wt % PYD2 482 nm 10.0%*1 4 30 wt % PYD2 482 nm  8.9% *1 8 30 wt % PYD2 482 nm 10.1% *1 9 30 wt% PYD2 490 nm 15.6% *1 10 30 wt % PYD2 480 nm  9.8% *1 11 30 wt % PYD2481 nm  9.9% *1 1 30 wt % PYD2 492 nm  8.9% *2 1 30 wt % PYD2 468 nm 7.0% *3 1 30 wt % PYD2 469 nm  7.1% *4 1 30 wt % PYD2 470 nm  7.1% *5 330 wt % PYD2 467 nm  8.2% *2 4 30 wt % PYD2 467 nm  8.0% *2 6 30 wt %PYD2 469 nm  7.0% *2 8 30 wt % PYD2 465 nm  6.4% *2 9 30 wt % PYD2 495nm 12.6% *2 10 30 wt % PYD2 466 nm  7.9% *2 11 30 wt % PYD2 467 nm  8.9%*2 *1:ITO(50)/HAT-CN(60)/TrisPCz(30)/host(5)/EML(30)/SF3-TRZ(10)/SF3TRZ:Liq =7:3 (30)/Lig(2)/Al(100) *2:ITO(50)/HAT-CN(60)/TrisPCz(30)/host(5)/host:compound.x:TBPe =69.5:30:0.5(30)/SF3-TRZ(10)/SF3TRZ:Liq = 7:3 (30)/Liq(2)/Al(100) *3:ITO(50)/HAT-CN(10)/α-NPD(15)/TrisPCz(15)/host(5)/host:compound.x:TBPe =69.5:30:0.5 (30)/SF3-TRZ(10)/TRZ-1DPBF:Liq = 7:3 (30)/Liq(2)/Al(100) *4:ITO(50)/HAT-CN(10)/α-NPD(15)/TrisPCz(15)/host(5)/host:compound.x:TBPe =69.5:30:0.5 (30)/mTRZ-1DPDF (10)/TRZ-1DPBF:Liq = 7:3 (30)/Lig(2)/Al(100)*5:ITO(50)/HAT-CN(10)/α-NPD(15)/TrisPCz(15)/host(5)/host:compound.x:TBPe =69.5:30:0.5 (30)/TRZ-4DPBT(10)/TRZ-1DPBF:Liq = 7:3 (30)/Liq(2)/Al(100)

1. A compound of Formula:

wherein R¹, R², R³, R⁴ and R⁵ are independently selected from hydrogen,deuterium, A¹, Ar¹, and D¹; only one of R¹, R², R³, R⁴ and R⁵ is A¹; atleast one of R¹, R², R³, R⁴ and R⁵ is D¹; A¹ is independently selectedfrom CN, fluoroalkyl,

X^(A) is independently selected from O, S, and NR^(A)′; R^(A) isindependently selected from hydrogen, deuterium, halogen, cyano,substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy,substituted or unsubstituted heteroaryl, substituted or unsubstitutedheteroaryloxy, and silyl; two or more instances of R^(A) taken togethercan form a ring system; R^(A)′ is independently selected from hydrogen,deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; two ormore instances of R^(A)′ and R^(A) taken together can form a ringsystem; R^(A1) is fluoroalkyl; L^(A) is independently selected fromsubstituted or unsubstituted arylene, and substituted or unsubstitutedheteroarylene; wherein each instance of arylene and heteroarylene can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; two ormore of these substituents taken together can form a ring system; D¹ isindependently selected from

X^(D) is independently selected from O, S, NR^(D)′, C(O), substituted orunsubstituted methylene, substituted or unsubstituted ethylene,substituted or unsubstituted vinylene, substituted or unsubstitutedo-arylene, and substituted or unsubstituted o-heteroarylene; whereineach instance of methylene, ethylene, vinylene, o-arylene oro-heteroarylene can be substituted with one or more substituentsindependently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl; R^(D) is independently selected from hydrogen,deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted alkoxy, substituted or unsubstituted amino, substituted orunsubstituted aryl, substituted or unsubstituted aryloxy, substituted orunsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy,and silyl; two or more instances of R^(D) taken together can form a ringsystem; R^(D)′ is independently selected from hydrogen, deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl; two or more instances ofR^(D)′ and R^(D) taken together can form a ring system; L^(D) isindependently selected from single bond, substituted or unsubstitutedarylene, and substituted or unsubstituted heteroarylene; wherein eachinstance of arylene and heteroarylene can be substituted with one ormore substituents independently selected from deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted aryl, and substitutedor unsubstituted heteroaryl; two or more of these substituents takentogether can form a ring system; Ar¹ is independently selected fromsubstituted or unsubstituted aryl and substituted or unsubstitutedheteroaryl without containing any nitrogen atoms; and wherein eachinstance of aryl, and heteroaryl can be substituted with one or moresubstituents independently selected from deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted aryl, and substitutedor unsubstituted heteroaryl without containing any nitrogen atoms; twoor more of these substituents taken together can form a ring system; andeach “*” represents a point of attachment to a carbon of the pyridinylcenter. 2-8. (canceled)
 9. The compound of claim 1, wherein A¹ isselected from

10-11. (canceled)
 12. The compound of claim 1, wherein R¹ is A¹.
 13. Thecompound of claim 1, wherein R² is A¹.
 14. The compound of claim 1,wherein R³ is A¹.
 15. The compound of claim 1, wherein when R² is A¹, atleast one instance of R¹ and R³ is not H; when R³ is A¹, at least oneinstance of R² and R⁴ is not H; or four of R¹, R², R³, R⁴, or R⁵ are notH. 16-17. (canceled)
 18. The compound of claim 15, wherein none of R¹,R², R³, R⁴, and R⁵ are H.
 19. The compound of claim 1, wherein D¹ is

20-21. (canceled)
 22. The compound of claim 1, wherein L^(D) is a singlebond.
 23. The compound of claim 1, wherein L^(A) is a substituted orunsubstituted arylene.
 24. The compound of claim 1, wherein Ar¹ isindependently selected from


25. The compound of claim 1, wherein Ar¹ is independently selected fromsubstituted or unsubstituted phenyl, substituted or unsubstitutedbiphenylenyl, and substituted or unsubstituted terphenylenyl.
 26. Thecompound of claim 1, wherein the compound is selected from

27-30. (canceled)
 31. The compound of claim 1, wherein the compound isselected from

32-38. (canceled)
 39. An organic light-emitting diode (OLED) comprisingthe compound according to claim
 1. 40. An organic light-emitting diode(OLED) comprising an anode, a cathode, and at least one organic layercomprising a light-emitting layer between the anode and the cathode,wherein the light-emitting layer comprises: a host material; and thecompound of claim
 1. 41-44. (canceled)
 45. A screen or a displaycomprising the compound of claim
 1. 46. A method of manufacturing anOLED display, the method comprising: forming a barrier layer on a basesubstrate of a mother panel; forming a plurality of display units inunits of cell panels on the barrier layer; forming an encapsulationlayer on each of the display units of the cell panels; and applying anorganic film to an interface portion between the cell panels; whereinthe organic film comprises a compound of claim 1.